Kingdom Of Prep

book by Maggie Bullock ISBN:0063042649 about J. Crew



I discovered that it was a story of not one but two cults of personality.

Everybody knows about one of these: Mickey and Jenna

But almost nobody outside of J.Crew’s inner circle remembers the other pairing

J.Crew’s father-daughter founders, Arthur Cinader and Emily Cinader (now Emily Scott).

Each of these duos would lead J.Crew to a golden period. Each would lead J.Crew to crash and burn, too.

I had loved it, too, for ages. Ever since boarding school

Chapter 1: “How to Be Really Top-Drawer”

October 1980. Twenty-one-year-old Lisa Birnbach

Every day, the numbers for The Official Preppy Handbook shot higher

But if The Official Preppy Handbook was a joke, it was more than that, too

I was bent on explaining the context of everything,” Birnbach told me. “To me the stuff was only interesting if you knew why the stuff.”

One of the book’s biggest influences had been Animal House, the monster movie hit of 1978

But what many people didn’t realize was that Animal House was a takedown of prep from within—made by a bunch of humorists who cut their teeth at the Harvard Lampoon

Birnbach was a smart-mouthed private school kid who grew up in Manhattan, graduated from Brown

The Handbook turned out to be an unironic hit. As Tommy Hilfiger, another insider-outsider who made a fortune on the aesthetic, would note, “Preppy travels so well.”

PREP GOT ITS START IN THE KIND OF SEPIA-TONE SCENE WE NOW associate with Hollywood backlots. Picture it: 1818

The merchant Henry Sands Brooks, seeing strivers with money in their pockets and a new need for the look of “respectability”—but with neither personal tailors nor the time to sit around waiting for a suit to be custom made by one—opens his emporium

Brooks Brothers’ two biggest breakthroughs

First, at the turn of the twentieth century, came the No. 1 Sack Suit—its unstructured shoulder and looser shape considered hair-raising at the time

Shortly thereafter, Brooks devised the oxford-cloth button-down shirt

But by the 1910s and ’20s, the prep pendulum had taken its first major swing. The Brooks Brothers look, originally intended to make the look of belonging attainable to the American everyman, had been adopted by fashionable youth, eager to shake out the starch of their fathers’ generation. Brooks Brothers was de rigueur at prep schools and colleges of the Northeast

If the look had a name at all, it was referred to as “campus” or “collegiate” dress

The sacred, secret ingredient to this recipe was one that a striver could easily miss. It wasn’t enough to wear the right things—you had to wear them the right way. Even in 1933, looking like you tried too hard was a kiss of death. Pulling the look off required a studied negligence. What the Japanese call wabi sabi. What the Italian Baldassare Castiglione pegged as sprezzatura in the sixteenth century

When prep’s pendulum swung back to egalitarianism in the 1950s, it was not because of some style whim, but because of a piece of legislation. Between 1945 and 1957, the G.I. Bill

On campus, where jackets and ties were still required for class, the well-established “collegiate” look did the trick

you got a bona fide fashion trend: a clean-cut, optimistic wardrobe sold at the one-stop “college shops” that popped up in department stores across the country

Yet what did everybody call it, in the ’50s? “Ivy style.”

What that meant was that, among Ivy Leaguers, “authenticity” mattered more than ever. Details separated the insider from the arriviste

In 1955, Miles Davis walked onstage at the Newport Jazz Festival in a boxy striped seersucker sport coat and bow tie purchased from tailor Charlie Davidson, whose Andover Shop sat right on Harvard Square in Cambridge

In 2021, the book Black Ivy captured Black leaders in the ’50s and ’60s from the worlds of literature (James Baldwin), film (Gordon Parks), and music (Thelonious Monk), in whose hands Ivy style looked inimitably chic—and politically forceful. These men weren’t appropriating the style “out of a desire to be white, coming from a deep sense of inferiority,” or as a “sign of conformity and compliance,” writes author Jason Jules. “Black Ivy was a kind of battledress, a symbolic armor worn in the nonviolent pursuit of fundamental change.”

But that came to a quick end. In 1965, Malcolm X was assassinated.

An anticonsumerist, antiestablishment revolution was here. On campuses awash in tie-dyed tees and paramilitary jackets, dusty dining-hall dress codes were out the window

A LITTLE MORE THAN A DECADE LATER, LISA BIRNBACH WAS DEBATING whether to quit her job at the Village Voice to work on some silly stocking stuffer of a book. What she could not have known was that in 1981, America would inaugurate Ronald Reagan.

it was in 1967—the very year Christian Chensvold cites as the death of prep—that Ivy’s ultimate arriviste founded his empire selling luxe, ultrawide ties. He was born Ralph Lifshitz, younger son of a Jewish émigré artist and painter from Pinsk, Belarus. Restyled as Ralph Lauren, he was savvily repackaging the fantasy he’d harbored as a kid in the Bronx

By ’69, even as Woodstock shook the universe and 250,000 Vietnam War protestors marched on Washington, Lauren was turning out buckle-back white linen trousers and anchor-print shirts

And Lauren wasn’t afraid to step on his forebears, either. In 1972, his Polo pony came galloping right for Rene Lacoste’s sacrosanct crocodile

But did Ralph Lauren make the cut for The Original Preppy Handbook? Nope

HANDBOOK-ERA PREP MANAGED SOMETHING THAT NEITHER THE campus style of the 1920s and 1930s nor the Ivy look of the 1950s had bothered to do: It invited women to the party

in the ’80s, women were acknowledged as full-fledged prep consumers

With women flooding the workplace

Fashion scholar Patricia Mears, the deputy director of the Museum at the Fashion Institute of Technology

In prep, Mears saw not the power of looking like a “richie,” but the safety of looking correct—like she belonged in a corporate world in which most women had hitherto appeared only as secretaries

Who was going to clothe these prep-hungry hordes?

almost nothing about Arthur Cinader—owner of a downmarket, family-run catalogue based in the fashion no-man’s-land of Passaic, New Jersey—indicated he was the guy for this job

Chapter 2: Cognitive Dissonance

the Botany Worsted Mills, a grim-looking complex of Victorian-era factory buildings sprawled across thirty-seven acres of Passaic

house dozens of companies. One of these was Arthur Cinader’s Popular Club Plan

young catalogue executive named Ted Pamperin

October 1981

about to interview with a man well-known in the catalogue business as eccentric, combustible, unpredictable. Arthur Cinader was said to be brilliant, but a bear to work with

Pamperin was here because both he and Arthur Cinader wanted to build something new, something different—something ambitious

Popular Club Plan was founded in 1947 by Arthur’s father, Mitchell Cinader, and a cousin, Saul Charles, a modest enterprise that started out selling candy by mail order

sold via a model called “party plan selling.” It was a bit like Avon or Tupperware

What made the company tick, though, was the way its customers paid: in small weekly installments spread over months

the business model had only really taken off in tight-knit Irish, Italian, and Polish communities of the Northeast, where families knew their club secretaries from church or work. Arthur wanted a new offshoot

What kind of enterprise would have that kind of payoff? In the end he settled on one close to home: a catalogue

Pamperin—who had started catalogue businesses for General Mills before moving to the Minneapolis-based mail-order family of Fingerhut


But by the early 1970s, with malls mushrooming across the country, catalogues had largely lost their luster

But shortly before Ted Pamperin arrived in Passaic, a rush of infrastructural and societal change had changed the math on mail order

for most smaller companies, catalogues cost too much to produce and post to be a get-rich-quick scheme.

But now we had MasterCard!

mail-order customers could pay instantly, over the phone—using an 800 number. Long-distance calls had long been a luxury, but the new 800 number meant customers could order for free

Even the humble zip code—first introduced in 1963—had a part to play: with zip codes, retailers could presort their catalogues in-house, dramatically cutting the cost of mailing

college graduating classes had reached fifty-fifty gender parity.4 Women were starting to see work as a career, not a stopover between school and motherhood.*

“having it all” would leave precious little time for browsing at Bloomies. But a catalogue . . . now that, a woman could peruse anytime, anywhere.

The early-’80s mail-order boom this all added up to was not so different from the revelation of online shopping that would dawn some fifteen years later

when Arthur hired Pamperin, all he knew was that he wanted to make a catalogue. What kind of catalogue? Pamperin’s first task was to answer that question

Behind Door No. 1: computer gear

Behind Door No. 2: prep

you had L.L.Bean and Lands’ End, both killing it in ’81.

What about a catalogue that sold the dream, at a price that was in step with reality?

After much deliberation, Arthur went with Door No. 2. Pamperin recalls this as a decision based not on a passion for fashion, or for prep, but on straight business sense: Popular Club Plan knew how to source, photograph, and sell apparel

“If Ralph wouldn’t do it, we won’t do it,”

First, though, they needed a name

Who came up with J.Crew?

As Pamperin recalls, it went like this: “If Ralph owns polo, why don’t we claim crew?”

little hints that one among them, Arthur himself, knew the codes of prep better than he let on. It was Arthur, for instance, who knew from the get-go that their fledgling company needed a backstory, a plausible-sounding fiction they could anchor the idea to

Arthur invented a history out of thin air: The company had started out as a men’s haberdasher in Princeton

Chapter 3: Puzzle Pieces

Photographer Michael Belk has never forgotten his first meeting with Arthur Cinader and Ted Pamperin. Belk was a tall, natty Southerner who shot for the menswear brand Gant

his photos were vivid, active, and shared enough of the glossy, inside-the-gates vibe of Ralph Lauren ads that Belk once received an irate letter from the agent of photographer Bruce Weber

Arthur Cinader was a student of everything, a voracious reader and observer

He knew about business, finance, consumers, computers, architecture—you name it.

Arthur knew how to manage a business, how to get the most out of people, how to minimize risk, how to consider a problem from every conceivable angle. “It was interesting to watch him work, and think.”

TED PAMPERIN AND THE TEAM SPENT MORE THAN A YEAR IN startup mode, building the guts of a new company

J.Crew bought many of its original names, or “prospects,” from the lists of L.L.Bean and Talbots

Brokers would print these rented addresses on a magnetic tape that was sent straight to the catalogue’s printer. The tape would only work for one printing, limiting access to those names to a single issue

Anybody who placed an order from that issue was added to an ongoing house list, and would become an MVP—someone who now received every J.Crew mailing

What would the new J.Crew sell to the people who, so far, were just names on an expensive piece of tape? So many cultural factors were at work in that decision! Annie Hall had come out a few years earlier, and unisex dressing was big in the ’80s

Most of the clothes J.Crew sourced were identical for men and women

J.Crew courted the active weekender: rugby shirts, henley shirts, a boatload of what it called “fieldhouse sweats,” and of course a polo shirt—cheaper than Ralph and Lacoste, but virtually identical

J.Crew had yet to hire a single designer—that expensive, time-consuming investment would come later, if they had staying power—so in the beginning, they sold private-label clothing

Plus a few recognizable brands sprinkled in for authenticity, like Boston Traders button-downs, Sperry Top-Siders, Woolrich trousers.

it wasn’t all that different from the bright, colorful basics of Lands’ End. Belk’s job was to make it feel different

Pamperin called up the University of Pennsylvania and offered to make a donation to its crew club, in return for access to an Ivy League boathouse and even a few college rowers thrown in as background players

Most of Arthur Cinader’s bio appears, on the surface of things, about as “J.Crew” as the Botany Worsted Mills itself. He was born to a working-class Jewish family in the Bronx, that old New York of stickball games and elevated subway cars—a familiar tune in American fashion, shared by not just Ralph Lauren (born 1939), but also by Calvin Klein (1942), and Millard “Mickey” Drexler

He was born to Mitchell and Sadie Cinader in 1927, enrolled at age thirteen in the brand-new Bronx Science—still one of the city’s most elite public schools (Mickey Drexler would enroll there two decades later

How does a man with neither a high school nor a college diploma enroll in medical school at Yale?

Arthur knew that back home, a new family business had bloomed. After three years, he left Yale, capping his lifetime graduation at 0 for 3

headed to Popular Club Plan.

In all the months Ted Pamperin was cold-calling Ivy League crew clubs

Arthur never said, “Well, when I was at Yale . . .” or “On our family vacations on Nantucket . . .” or “At my daughters’ prep school . . .”

Yet at the end of the day, Arthur did not drive home to some suburban New Jersey house. He returned to 1185 Park Avenue, one of the most distinguished addresses in Carnegie Hill. He loved English-style horseback riding. He collected art; by 1956, he had already loaned his Jackson Pollock for the artist’s one-man show at the Galleria Nazionale d’Arte Moderna in Rome.

Arthur was, like Lisa Birnbach—like Calvin Klein, like Ralph Lauren, like Mickey Drexler—an insider-outsider


it was time to make the sausage. Here, Michael Belk was a full-service operation: He not only shot the lifestyle photography but also brought in an art director to design the pages

Ted Pamperin, whose name has since been erased from the annals of J.Crew history, laid most of that initial groundwork. But there was one part of that first issue that Arthur dug into. He toiled for weeks on the copy.

Emily Cinader walked in the door in January 1983, a month after collecting her diploma, and just as the first issue was on its way out.

Quality for the long pull, read Arthur’s labored-over copy. The heritage of J.Crew weekend clothes is 100 years of outfitting rugby, lacrosse, and crew. Whence their long-wearing construction. And authoritative style.

Chapter 4: Girl, Boss

If J.Crew had just fallen on its face, it wouldn’t take long to find out. When a new catalogue clicks with customers, the orders come in fast, arriving a day or two after it lands in mailboxes. When it doesn’t, a tepid response says it all. You can usually tell if you’ve got a success on your hands within seventy-two hours. By the end of J.Crew’s first week, its new bank of telephone operators were inundated

breaking even within roughly eighteen months

Change was afoot at J.Crew. In 1984, Arthur hired a new merchant, Carrie Stone. She recalls that in her first interview, the C.E.O. “made it clear that it was my job to train his daughter to be president of the company eventually.”

She might have been young, but she was already discerning; Stone recalls her innate eye for style and quality, her instinct for what “was” and “wasn’t” J.Crew—and her willingness to speak her mind

Emily possessed something most others at the J.Crew table sorely lacked: firsthand knowledge of the young, outdoorsy, preppy life.

Emily knew that to be cool, J.Crew needed people who were cool: young, talented creatives, not from other catalogue businesses but from the realm of fashion.

It wasn’t long before Emily had assumed responsibility for the look and feel of J.Crew, selecting models, bringing in new photographers, choosing shoot locations, and—despite her total lack of design experience—taking the lead on hiring J.Crew’s first in-house design team

The J.Crew that fans from the ’80s and ’90s still harbor such nostalgia for today? That was 2.0: Emily’s J.Crew.


Emily was super beautiful

Horne was an assistant editor at Vogue

That night, she wanted to know everything about Horne’s job at Vogue. How did the shoots work? How was the styling put together?

Emily called the front desk of Vogue and asked to speak to Horne: Would she come work for J.Crew?

Horne wasn’t sure what she’d been brought here to do. Emily had a gift for spotting talent and was aggressive in pursuing it, but she wasn’t a big one for spelling out the mission. Lots of people would come to work at J.Crew for the very reason Tierney Horne just had—because there was something about Emily

J.Crew was not the first to pioneer what we would soon call “lifestyle photography”—far from it. If you had to pinpoint the birth of that invention, the summer of 1977 would be as good a time as any. That’s when the up-and-coming Bruce Weber booked the model Jane Gill to play a preppy girl in a group of all-American college guys.

Back in New York, Weber took the images to Lauren, who according to Gill was instantly on board: This is what I want to do!

At the dawn of J.Crew, Ralph Lauren ads were a thing.

once the newness of the Ralph look began to rub off, you had to admit, his models did look a little morose

vaguely costume-y, a little camp

J.CREW LEAPT INTO 1985, THEN 1986, THEN 1987, WITH A SENSE of unbridled potential

Budget mattered, as did efficiency. J.Crew didn’t shoot single ad campaigns, but rather books of one hundred–plus pages, fourteen times a year, showcasing hundreds of items each time. To pull this off, they had to pioneer a new way of shooting.

Horne began styling a whole group of models in layers, so they could peel clothes off as the day went on. “I’d put on a T-shirt, then a polo shirt, then a chambray, then a jacket,” she says. “I’d layer the shit out of everybody, and then we’d give them a task: Okay, make pancakes over an open fire. So there you’ve got your jacket photo.”

She borrowed vintage luggage from T. Anthony, antique watches from Upper East Side jewelers. Shooting things that weren’t for sale? This was how magazines worked—not catalogues.

Their other secret: J.Crew was always in motion. For every shoot, there was a destination, and for every destination there were activities

All that activity kept models from looking like “catalogue people,” those cardboard cutouts who existed solely to sell you things

These photos ran “full-bleed”—that is, stretched across a whole page

Back at the office, for years to come, the litmus test of a great J.Crew picture was: Does it feel real? Could it pass for a snapshot?

herding whole teams of “friends” and dozens of body bags stuffed with clothing up the side of a mountain in frigid predawn darkness, pitching tents in the snow, all so you’re ready to begin shooting at first light—that’s next-level effort. That serene ice-skating shot didn’t just require a picturesque little pond; it required hiring locals to shovel two feet of snow off the pond before the sun came up

ALL ALONG, AS EMILY WAS HIRING PEOPLE TO IMPROVE J.CREW’S photos, she was simultaneously fixing the clothes those photos featured.

Rewind back to 1984. In her early days, Emily elevated the product range as best she could—mostly by bringing in things to copy, sometimes as an outright knockoff

In 1985, Emily hired designer Linda Snyder

Not one of them was over the age of twenty-seven, and most had only a few years’ experience

This core team churned out a handful of designs that, for a certain generation of believers, still define J.Crew

these were things the designers longed for in their own closets. One by one, they zeroed in on specific essentials they wanted to perfect

Some of J.Crew’s greatest hits were relatively subtle improvements on existing items from the canon

THE FIRST TIME EMILY WAS CERTAIN J.CREW WAS A BONA FIDE hit, it was because of a photo of Jane Gill—yes, star of the Ralph Lauren campaigns.

Emily was a stickler for texture, she cared how clothes felt almost as much as how they looked. Plus J.Crew had perfected a way of wearing clothes, a host of little throwaway styling tips that made them cool

In that fateful photo of Gill, she’s wearing nothing more elaborate than a pale pink T-shirt. Her smile is partially shaded by a wide Stetson, and—of course—there’s a tiny Jack Russell nestled in her arms.

had finally struck gold. Whatever the reason, that photo had an effect that today would be called “breaking the internet.” Emily had gone into it thinking the T-shirt would be a success, so she ordered what was for J.Crew a large amount, five thousand. But then eighty thousand orders poured in.

Chapter 5: Hooked on a Feeling

By the late ’80s, J.Crew was a thing.

Customers loved the outfits so much, they began to order every item on a model’s body

In 1989, Kelly Hill was a coed on the grassy, redbricked campus of Virginia’s James Madison University. Among her cohort, the arrival of a new J.Crew catalogue was an event. Back in their dorm, Hill’s roommates enacted a ritual that had nothing to do with shopping: reading the J.Crew catalogue like a bodice ripper from the supermarket checkout.

J.Crew was no mere catalogue. “J.Crew was a movement,*

the spell Arthur was weaving would last a lot longer than those first pictures. From the first issue, a J.Crew polo shirt wasn’t blue, it was copen blue. Corduroys came in palamino, cedar, and nutmeg

He hired excellent copywriters—again dispatching recruiters to the Ivy League: no degree too exalted for a future bottom-rung J.Crew caption writer! But he policed their words until, in the end, he might as well have written every syllable himself

As J.Crew grew into itself, Arthur became more of an essentialist in regards to the copy

When the J. Peterman catalogue came along in 1987, it took highfallutin’ copywriting to a comical nth degree

SCOTT FORMBY, THE DESIGNER SO UNEXPECTEDLY WON OVER BY Arthur, turned out to be an even better fit for Emily. By the time Formby arrived at J.Crew, Ted Pamperin was long gone. By 1986, Pamperin had seen the writing on the wall: no matter how astounding the launch of J.Crew had been, Arthur was never going to give him an ownership stake. After Pamperin, Emily was named president of J.Crew. She was twenty-six at the time.

By 1988, Emily had achieved J.Crew 2.0: the company had its own aesthetic, and sold a handful of wear-forever pieces that people loved.

Formby would help her tackle 3.0.

In their first conversation, “we talked a lot about our favorite companies,” Formby recalls. In this conversation, Ralph Lauren never came up. To Formby’s surprise, and his great pleasure, Emily shared his love for small, cool European companies like A.P.C. and agnès b. that were selling elevated, simple clothes—“basics, the way we liked to dress,” Formby says—that felt newly of the moment

Could we do something as important as that: not over-designed, and still relevant, but more for an American market?”

one word Emily and Formby did not use, ever? Preppy

We were cool. Preppy wasn’t cool.”

Emily had spent her early adolescence not in the preppy Northeast but in the high desert city of Albuquerque, NM

The goal wasn’t to sell entry-level elitism; indeed, they envisioned J.Crew as an alternative to that kind of thinking.

Maybe it makes sense that Emily was a preppy denier. One seemingly reliable litmus test of a true prep: Does she say she’s not?

Chapter 6: 625 Sixth

Emily once sent an assistant back to the mat for some sixteen days until she found a name Emily was willing to approve for a single shade of green

It was Emily who had insisted J.Crew move, at last, to New York City. If they were going to compete for talent, stake a place in the industry firmament, they couldn’t do it from New Jersey. In 1988, J.Crew left its slightly embarrassing older stepsister, Popular Club, behind and took over two floors in 625 Sixth Avenue, on the corner of Nineteenth Street in Chelsea

There was no more leaving at a decent hour; they worked feverishly, stayed late, came in on weekends—whatever it took.

Working there was fun. “There was a belief in what we were doing, and the work ethic was insane,”

And Emily, now twenty-eight, was their absolute center of gravity, working thirteen-hour days

She felt symbolic of something bigger, too, at what seemed to be a turning point for the working woman

She was exquisitely disciplined, rigorously efficient. Long before the gym became a fixture of modern life, she worked out with a trainer and practiced yoga. She shared Arthur’s hypersensitivity to noise. Women took off their bracelets before walking into her office; she couldn’t stand the clattering

Emily had zero shame about demanding the conditions she needed to operate

Scanning the landscape for someone to compare Emily to, many latch on to Vogue editrix Anna Wintour

Like Wintour, Emily wasn’t about to change to try to please anybody

Emily wasn’t the kind of creative director who throws hissy fits and hurls scissors across the atelier—and fashion had plenty of those. She was just highly specific

In truth, most people at J.Crew were a little in awe of Emily

BY THE CLOSE OF THE ’80S, THE FIRST WAVE OF CUSTOMERS WHO had fallen for J.Crew in high school and college were getting jobs, buying homes, having kids. Going to work. J.Crew already owned their weekends. Emily wanted to get her hands on their nine-to-five lives

She would target this woman with Classics, a new range of tailored jackets, trousers, office sheaths. If Classics went over well, Emily had an even more luxurious and unabashedly pricey range in the pipeline. That one she called Collection.

How to convince people to buy silk blouses and $350 jackets from the catalogue that made their favorite $15 tee?

Emily hired a new photo director, Therese Ryan Mahar

Soon, J.Crew shoots would not by definition include puppies and hay bales; they would be staged on city streets, in photo studios, at train stations, and sidewalk cafés

Mahar’s first big assignment: find a model for the cover of the Fall 1989 catalogue, which would debut the new Classics range

Linda Evangelista was already a favorite of Chanel’s Karl Lagerfeld and Italian Vogue snapper Steven Meisel.

For six months, Mahar pestered Evangelista’s agent at Elite, with no luck

tracked down Evangelista herself

After some long-distance pestering, Evangelista gave in, with palpable reluctance. “Probably just to get me off the phone,” Mahar recalls with a laugh.

Mahar took that yes to the studio of Vogue photographer Arthur Elgort—as big a get for J.Crew as Evangelista herself.

How many permutations of this woman had fashion lovers already seen? But this one, somehow, felt like the “real” Linda

For years, Elgort would shoot the American icon Lauren Hutton for J.Crew

Chapter 7: Malls of America

With the ’90s ushering in a new, hypercompetitive mall culture, J.Crew’s exhilarating upward climb was in danger of sputtering out

after six years of “explosive” growth of 25 to 30 percent a year, J.Crew’s mail-order business was expected to grow by just 15 percent in 1990

The impending slowdown was way bigger than J.Crew

the mail-order industry had grown 12 percent or more a year, outpacing any other form of retail three to one. But by ’88 it had plateaued, growing by less than 1 percent

Tweeds, a popular new rival that melded prep with a velvet-leggings Euro vibe, had been founded by none other than Ted Pamperin, with the help of a crew poached largely from J.Crew

When J.Crew launched, catalogues had been the thing. But anybody who’s ever watched an ’80s movie knows that in the ensuing decade, American life revolved around a new playground: the mall. We were living in a material world

The indoor shopping mall was born in the ’50s, as a radical proposition by architect Victor Gruen, an avant-garde Viennese socialist

Gruen’s intentions were idealistic; he saw the mall as a solution to the cultural wasteland of suburban sprawl

In later years, faced with the consumerist revolution he had unwittingly wrought, Gruen would disavow his invention

But by the mid-’70s they had become old-fashioned, dated, she said—like suburbia itself. Surely the mall was on the way out. Didion must have been shocked, then, when the opposite occurred. In the ’80s, the mall went into overdrive*

in the ’80s, clothing became increasingly tribal, a public declaration of your taste

took a lot of shopping

“Like it or not, the mall offered access to a broader world than flyover country could easily access,” author Ian Bogost wrote

To compete in this climate, J.Crew needed stores. Lots of stores. For decades, department stores had been the mall’s main attraction, the anchor that brought foot traffic to the smaller boutiques. But in the ’80s, the department store had already begun its long, slow decline. The name of the game was “specialty-apparel retail” (soon just “specialty retail”), i.e., Gap, Aéropostale, Banana Republic, the Limited, and Benetton

Specialty retail was arguably a child of the ’60s, born in Columbus, Ohio. That was where Leslie “Lex” Wexner first envisioned a chain of smart-looking shops that sold a single label

J.Crew, too, had a brand. Arguably a great one. But it was seriously late to the specialty retail party. And while Arthur and Emily were catalogue savants, neither had a whit of experience in stores.

Would J.Crew, the store, even work?

Absent the carefully constructed context of its photos—the touch-football games, the bobbing sailboats—and viewed for the first time under dressing room fluorescents

Arthur was ready to take that risk

he needed a new lieutenant. Arnie Cohen was a charismatic young gun, palpably brimming with ambition, plus a little something extra—a kind of eager, wheeler-dealer energy

In a poetic prep twist, the site Cohen zeroed in on for J.Crew’s first store was located mere blocks from the first outpost Brooks Brothers established in 1818. South Street Seaport

was basically a middle-American mall clinging like a barnacle to the edge of Manhattan, a long way from anything that could be considered fashion. But it had two things going for it. After work, a surge of suits from nearby Wall Street swept over the area like a human wave

They had worried J.Crew’s je ne sais quoi would be lost in translation, but they found the opposite was true. The store offered something the catalogue could not: instant gratification

J.Crew would never have The Gap-level billions to fuel expansion. But at least now they had a track record, evidence that J.Crew stores did work

thanks to the catalogue, he knew exactly how many J.Crew customers lived within a ten-mile radius of Chestnut Hill, how many times a year they purchased

Back in Manhattan, Emily’s design team did not operate with the Ivy League on the brain. They considered cliché, textbook prep gauche, outdated. Increasingly, their energies were turned to timeless

Yet even as Emily was steering away from the look (and implications) of pure prep, Arnie Cohen was planting her fine-tuned brand in well-to-do enclaves around the country, and the words Ivy League and preppy were the bull’s-eye of his sales pitch.

Chapter 8: California Girls

Less had always been more in Emily’s universe. And now, as fashion rounded the corner from the over-the-top ’80s into the minimalist ’90s, it was as if she had bent the style gods to her will

More and more women were dressing like Emily

By the time J.Crew debuted a new outpost in Dallas in 1992, the company had pivoted hard from the clubby “library of product” look of the Seaport store to an aesthetic that had Emily’s fingerprints all over it

If Belgian austerity was one side of ’90s minimalism, and office-drone khakis were the other—well, J.Crew found itself in a sweet spot between the two

A new, unsentimental concept, “uniform dressing,” had emerged; it made sense to minimalists, but also to a new class of time-crunched professionals

certain pragmatism about price, too. “There was some notion that if you were buying your T-shirt at the Gap as opposed to from Helmut Lang, you were getting the essence of something. It was a reverse snobbery about basics—this idea that you’re not a sucker, right?”

Many expected that if Emily ever settled down, it would be with some clean-cut, all-American scion with a very nice sailboat. Someone who looked like the J.Crew guy. Cary Woods, then, presented a real head-scratcher. He was a kid from the Bronx—sound familiar?—who’d made it big in Hollywood, first as an agent at William Morris, then as an executive at Columbia Entertainment

At twenty-one, with no money to speak of, and no great prospects ahead of her, Jenna Lyons had just turned down a job in high fashion—the kind of job most designers in her position would kill for. She wanted to make relatable clothes for “real” people.

she instinctively got the promise of J.Crew

As J.Crew settled into its ’90s sweet spot, it was becoming something it had never quite been before—oddly hip. Yes, they were nailing the look of the time. But this also had to do with Emily, who was now half of a Hollywood/Fashion power couple.

Emily, who had never seemed to find her tribe in New York, was hanging behind the scenes in a new milieu. J.Crew gone Hollywood?*

at some point questions began to arise about whether Emily’s head—always screwed on so tight—had been turned. Was her new scene impairing her judgment about J.Crew?... Such questions tended to focus on J.Crew Collection

It was helmed by a young designer named Lena Youm, who had been poached from Calvin Klein, and the Calvin imprint was palpable. Collection was trend-proof, luxurious, with a vaguely Katharine Hepburn slant—cuffed flannel trousers, well-cut camel coats

Could J.Crew’s little stab at luxury be a modest but influential hit? The idea was not totally out of the question.

some on the business side were significantly less devout. As far as they were concerned, the number one priority was growth

Chapter 9: Go Big or Go Home

Nineteen ninety-six

99 Prince was a historic building

Back in ’89, Arthur and Arnie Cohen had proclaimed that J.Crew would have fifty stores by 1994. Two years past that deadline, Cohen was long gone. They had thirty-six stores

Arthur had been known to treat his own retail division—the supposed engine of his company’s growth—as an ugly stepchild. He fretted about what he called the “parasitism” of the stores stealing business from the mail-order side

Exhausted and, perhaps, fallen out of favor, Cohen had left the company in 1993

competition was fiercer than ever

Emily was determined to go high. “We’re building a mini-Barneys, Dave,” she liked to remind Dave DeMattei, the president of retail she hired in 1995—the guy who, by the following year, was creeping around the basement of a building on Prince Street

she wanted DeMattei to open fifteen new stores a year, for a total of one hundred by the year 2000. The most important of these was Prince Street, a real New York flagship. A store with the potential to do for J.Crew retail what the Evangelista cover had done for the catalogue, seven years earlier: make the gatekeepers of style, trotting up and down the streets of SoHo, sit up and take notice.

In ’96, a twenty-year-old college dropout named Brian Sugar got the bright idea that the brave new world of online shopping was especially well suited to mail-order companies, which already had everything they needed to thrive on it: the photography, the merch, the order-fulfillment infrastructure. As Sugar saw it, for a company like J.Crew, going online was simply the logical next step.

Arthur Cinader Jr. first popped up around the offices of J.Crew a few years earlier, fresh out of college. He was smart, a little geeky

the youngest Cinader did have a sense of purpose. It just happened to be on a side of the business that fashion people tended to think very little about: tech.

The new news,” wrote the fledgling novelist MacKenzie Scott (then Bezos) to her mentor, Toni Morrison, in 1995, was that MacKenzie and her husband, Jeff, had moved to Seattle and started a business selling books on the internet

By the time Brian Sugar arrived, Arthur Jr. and an intern had put up a starter site

With Sugar building 2.0, there were existential questions to answer. This was not unlike the challenge Arnie Cohen and Arthur Sr. had grappled with years earlier, opening the first stores: How did you bring the aspirational J.Crew vibe into a new dimension—in this case, one distinctly lacking charm and warmth?

For eight months, Sugar spent every waking hour on the site. He was racing the competition.

Sugar had learned that at Gap’s San Francisco HQ a woman named Aileen Lee—now the Silicon Valley rock star behind V.C. firm Cowboy Ventures—was leading the charge to launch

There was already internal jousting between stores and catalogue. If a website did take off, whose business would it eat into?

MEANWHILE, ON PRINCE STREET, DAVE DEMATTEI WAS ROMANCING André Balazs, the insider’s insider who owned the storied Hollywood hangout Chateau Marmont. For years, Balazs had been making noises about turning 99 Prince into SoHo’s first boutique hotel, a newish concept at the time. He needed a retailer for the ground floor

In 1995, there were two different ambitious J.Crew spoofs.

Then, from the dark wizards of Spy, came “Crew,” a multipage parody that gave the J.Crew treatment to the gold chains and boxy flannels of what it called the “gangsta” look

It was time for J.Crew to really sell itself. Or rather, herself. Not just in the catalogue, but in the press. What ambitious American woman would not buy into Emily Woods? There was one problem: Emily fundamentally did not believe that J.Crew should have a “face.”*

Chapter 10: Five . . . Four . . . Three . . . Two . . . ONE

In the summer of 1997, Arthur, Emily, and a SWAT team of J.Crew execs zigzagged on flights across the country, taking a series of meetings that most people back at the office had no idea about—and that would forever alter the fate of J.Crew.

In 1997, they had forty-eight stores

Eddie Bauer and Victoria’s Secret had 385 and 737

To compete, J.Crew would have to open ten, twenty, thirty stores a year. That would take the kind of financial firepower that a bootstrapped company with modest profits doesn’t have

Plus, with Arthur approaching seventy, he needed a succession plan. His original shareholders—mostly family members, also in their golden years—were ready for their long-awaited windfall

The only way she could take over, and Arthur could exit, was by selling a chunk of J.Crew to the right buyer.

The number one question at every stop: How big can J.Crew get?

any investor scrutinizing the balance sheet could see at a glance J.Crew’s dirty secret: On some level, the company had never quite been what it seemed. It appeared to be a major hit of the ’90s, a golden brand that radiated prosperity. But as one retail veteran put it to me with a shrug, “Yeah, but they didn’t make any money.”

Sales of $808 million was nothing to sneeze at

the company cleared just $14 million in 1992. By ’96 that had sunk to $12.5 million

what Emily and Arthur were after was an investment firm. Someone to buy a chunk of the company, help them run it more efficiently, grow it fast—and then take it public, making back their investment (and Emily’s, as a part owner) many times over. Sounds simple enough, right? But J.Crew’s on-again, off-again relationship with the venture capital firm Texas Pacific Group would prove to be longer and more convoluted than a Hollywood love story. T.P.G. came to Emily through a buddy of Cary Woods*

Today, T.P.G. is among the biggest, most established firms in the V.C. world. But in 1997, it was a small, emerging firm said to be led by investors of a different stripe

founding partners David Bonderman and James Coulter, who met as investment advisors to billionaire Texas oil man Robert Bass

Bondo,” as he was known, had once toiled in the Civil Rights Division of the Justice Department; studied Islamic law in Tunis and Cairo8; and in the ’70s successfully argued before the Supreme Court to halt a wrecking ball poised to demolish the Beaux Arts facade of New York City’s Grand Central Terminal

In a leveraged buyout, T.P.G. would buy a majority stake for $560 million

valued J.Crew at almost ten times EBITDA. This was generous; it arguably bordered on overvaluation

could T.P.G. start the search for a new J.Crew C.E.O., whose appointment would be announced soon after the deal closed?

What if the deal blew up? Anything could happen. Rubel recalls, “He was not going to budge until the money had transferred.”

By the late ’90s, though, if Emily was ready to run J.Crew without Arthur’s interference, nobody would have blamed her

What really went on between Arthur and Emily invariably happened offstage

Arthur put his foot down. T.P.G. could put in a C.E.O. after it owned J.Crew—not before.

A DEAL ALMOST NEVER HAPPENED. BY FALL, J.CREW AND T.P.G. had at last made it to final talks when the third-quarter numbers came in. J.Crew had already taken a hit that August, when UPS shut down

J.Crew lost nearly $9 million in revenue on the strike alone.13 And that wasn’t all: The Fall 1997 catalogue had dud written all over it.

in an LBO the burden of that debt is not on the buyer—it’s on the company that’s been bought, which is now on the hook for fat quarterly interest payments, plus dividends to the new shareholders (in J.Crew’s case, largely T.P.G.) and costly management fees (also to T.P.G.) for the work of steering its new purchase.

LBO debt payments are often so hefty that a recession, or just a few dud seasons, can be all it takes to push it over the edge

Early that October, after the UPS strike and the dismal quarter, T.P.G. asked J.Crew to drop its price. This time, it was Arthur who had to bend.

Emily retained 12 percent of the company, with the option to buy more. She was getting a $10 million signing bonus, plus a five-year contract for $5 million

As for Arthur, it seemed he had retired

As for Arthur, it seemed he had retired. No one I spoke with recalled a formal announcement of Arthur’s departure.

not strategic. When Arthur vanished without acknowledgment—and without giving his formal blessing, toasting Emily at the helm—it was all too easy to believe the heated narrative that soon spread from desk to desk: that Emily, hungry for control, and sick of being under her father’s thumb, had ruthlessly ousted Arthur.

The reporters dutifully published these claims. But they also gleefully zeroed in on behind-the-scenes gossip: suddenly, Emily and Arthur’s lackluster people skills were public knowledge. Writer Warren St. John opened his profile of the “Ultimate J.Crew Gal” in the reliably catty New York Observer with “the fucking pumpkin story.”17

No man who ran a company “down to its nooks and crannies” the way Emily did would be expected to play nice all the time. “What’s wrong with saying, ‘the fucking pumpkin’?” Hill says.

T.P.G. muscle was already highly visible in the J.Crew offices. Dick Boyce had walked in on day one with an aggressive one-hundred-day playbook, determined to instill “discipline and predictability” in their product development process.18 Bain & Company already had boots on the ground, gathering data for a restructuring.

In late 1997, as its big opening act, T.P.G. handed out one hundred pink slips, axing 10 percent of J.Crew’s workforce

As weeks ticked by, it was painfully clear that the numbers these suits had come here to crunch did not look good. It turned out that third-quarter dip that had threatened to throw off the T.P.G. deal was just an amuse-bouche for a dismal holiday season

As 1997 drew to a close, revenue was $25 million short of what J.Crew had forecast to T.P.G. Cash flow had suddenly dried up.

at the company Christmas party

“The days of Mom and Pop running this business are over,” is how one HR exec recalls Bonderman’s brief but devastating speech. It was like some bad-joke version of the ghost of Christmas future: J.Crew had been inefficiently run, he told them, and things were about to change

Chapter 11: Swan Song

Chapter 11 Swan Song* The Spring 1998 catalogue was peak J.Crew*

Dawson’s Creek

But back at 770 Broadway, when that catalogue dropped, the mood was far from playful. That February, Emily introduced J.Crew’s new C.E.O., an affable, somewhat fatherly retail vet named Howard Socol

Socol looked great on paper. He’d just retired from running Burdines

He was said to be one of Federated’s best and brightest.3 But his vibe, to his new employees at least, was a little “garmento,”

most Collection staffers had been laid off in T.P.G.’s first round of layoffs. Its head designer, Lena Youm, was out a month after Socol’s arrival

Emily, watching the dissolution of her trusted inner circle and her airtight brand, needed to onboard the outsiders

Emily tapped Gayle Spannaus, the company’s longtime model booker, to do a classic branding exercise

Was the wall helpful? Unclear. Spannaus recalls that it did not stay up for long

this batch of consultants was here for something different: they’d been hired by T.P.G. to question senior staffers on the issue of Socol v. Woods

Over the holidays, Socol phoned senior staff at home: he was leaving. Emily had won this round. The tone of the press surrounding Socol’s departure, after a mere ten months*

he soon went on to helm a golden era at Barneys


T.P.G. had plucked him from the frozen foods division of Nestlé

Sarvary was a former Bain analyst, a finance guy

There was arguably a method to T.P.G.’s madness. For one thing, by the mid-’90s there simply weren’t that many great merchants on the market. The industry’s most celebrated “merchant princes” had traditionally been forged in the training programs of great department stores like A&S and Bloomingdale’s

Maybe it should not have come as a complete shock when she vanished altogether

In February 2000

“They’re letting me go,” Emily told Sharpe

If Formby and Sharpe mourned Emily’s departure, not every heart at J.Crew broke for her. Emily was the one who’d invited T.P.G. into their backyard in the first place—in the eyes of some, killing the magic of their brand. Now Emily had millions from the sale as a consolation prize, plus her dividend payments, while those who had served her were stuck holding together the pieces of a rapidly disintegrating brand.

Emily wasn’t gone gone. By 2001, her ownership stake was up to 19.2 percent; she’d remain board chairman until 2003

J.Crew was now officially “merchant led,” Sarvary said, issuing a string of market research–led dictates that sounded straight out of some reverse Ab Fab: The designers could no longer use orange—he didn’t “understand” the color. Green, too, was out: men did not wear it. Light blue, on the other hand, was a bestseller. So he wanted light blue in every color palette, and in the Christmas windows, and on the front table of every store.

But on the balance sheet, his approach appeared to be working

But that enviable balance sheet was the result of two-plus years of gradually cutting corners on quality, design, store design

In April 2002, J.Crew’s woes were outed in the New York Times. The headline said it all: “In a Race to the Mall, J.Crew Has Lost Its Way.”

the truth was that J.Crew was on the brink of defaulting on the staggering debt load of its 1997 LBO. The article left no ambiguity about who was at fault: T.P.G. had been “running the company as if it were selling car parts or copier paper,” draining J.Crew of all points of view.

Mark Sarvary was out by May.

they had a new C.E.O., Ken Pilot—arguably their most qualified appointee yet, having spent thirteen years at Gap

They’d already tried to offload J.Crew

American Eagle Outfitters had initially offered $650 million. But after due diligence, that shrank to $500 million—less than the company had been worth five years earlier, when it had almost a hundred fewer stores.

But there was another option. They could restructure J.Crew’s debt—taking on an even higher interest rate—to give the turnaround one last shot.

A new, very strong, reason to consider this option had just popped up on the horizon: Millard “Mickey” Drexler

six months before this meeting, he’d been unceremoniously axed. The best news for T.P.G.: he had walked away from a $2 million noncompete deal

Chapter 12: Rocket Man

J.Crew had never seen the likes of Millard “Mickey” Drexler. First and foremost, he was a dyed-in-the-wool stores guy, “a shopkeeper at heart,” he likes to say. Arthur and Emily had been catalogue makers to their core, struggling to make their mark on the American mall. Mickey built his legend at Gap Inc. by putting a store in every mall and on what felt like every street corner in the nation.

The man could have been bred in a lab to be the Cinaders’ polar opposite: He was a loud, irreverent, neurotic New Yorker—cliché, but in this case accurate—congenitally afflicted, he says, with shpilkes, a condition he jokingly describes as “Yiddish for ‘ants in my pants.’”1 But shpilkes is more than that—it’s a state of perpetual impatience, anxiety.

He describes himself as a shy, insecure kid—an observer, absorbing every detail. But not exactly meek. Mickey was allergic to authority

Bronx Science turned out to be both the greatest thing that ever happened to Mickey, and a fairly miserable experience.

At that school, college was a foregone conclusion. That certainty changed Mickey’s life. He was the only one of his cousins to go to college, graduating from SUNY–Buffalo, then enrolling at Boston University for an M.B.A.

Mickey’s other true love? Retail. He was part of a generation of great merchants that rose out of the summer program at the legendary downtown Brooklyn department store Abraham & Straus (later absorbed by Macy’s). The young men’s jeans department suited his shpilkes, but also his talents. Mickey had the right-/left-brain command of a true merchant: an instant recall of sales figures, but also an eye for beauty and a nose for longing

In 1976, he skipped over to Macy’s for $50,000 a year, enough to move the Drexlers to Park Avenue.8 The kid from the Bronx had arrived. But his love for department stores was waning. Mickey bristled at any hint of corporate bureaucracy

In 1980, he got his shot. At thirty-six, he was named president of Ann Taylor, then a lackluster, money-leaking chain of twenty-five stores

In a flurry of change, he trashed the brand’s existing clothes, image, design, and management, and built a new image from the ground up. For this he had one muse: Jacqueline Kennedy Onassis

Equally critical to the process: he shifted the company to vertical manufacturing and product development processes

In three years, he turned Ann Taylor into a legitimately hot property

This was just the kind of magic Don Fisher desperately needed over at Gap

Specializing in Levi’s made Gap the original “denim store” at a time when jeans had just become the 24/7 uniform of American youth.14 Gap soared through the ’70s,

Fisher’s company had lost its mojo just as the American mall had gone into overdrive. The specialty retail race was on—new contenders like Benetton and Esprit were on fire—and Fisher was just desperate enough to let Mickey take a swing

A YEAR AND A HALF LATER, ON AUGUST 15, 1984, MICKEY HAD his moment of truth

For years, Mickey had been mentally percolating the brand he would one day launch

that day in August 1984, new merchandise was set to hit some 450 Gap stores that had all been simultaneously remodeled to Mickey’s specifications—a feat that is almost unthinkable today. There was no soft launch, no trial and error, nothing

all because of that little word Mickey had printed on cards: Simplify. Well, that and the advertising.

Miles Davis wore khakis

These ads gave Gap something that no one but Mickey believed possible: actual cool

The underlying conceit: nobody was too good for Gap basics. But it was Sharon Stone who really drove that message home. In 2021

A day before the Oscars, Gap got a fax from Sharon Stone that read a little like a ransom note. It said that if the company would donate $250,000 to her sister’s charity, Stone would wear Gap to the Academy Awards the following night

Sure, Stone was wearing Gap, but how would anyone ever know it was Gap? Mickey was apoplectic

But the next morning, everything changed. The press was all over it. Decades later, images of Stone from that night regularly pop up on lists of the most iconic Oscar outfits of all time

That moment was the apotheosis of the ’90s craze for high-low dressing. As the writer Holly Brubach noted earlier, if your shirt cost $11.99 from Gap, it told the world you weren’t a sucker. Now that was cool

THE GREATEST SUCCESS OF MICKEY’S CAREER, THOUGH, WASN’T at Gap. Old Navy was born in 1993, after a rare lull in Gap’s rise

in 1991, he took a trip to Target to check out Everyday Hero, a new range that looked a lot like Gap lite.24 These were not terrible clothes, he realized.

Within four years, Old Navy was a billion-dollar brand

In 1995, Fisher ceded the C.E.O. spot to Mickey, giving him dominion over not just Gap but also Banana Republic, Old Navy, and Gap Kids.

In 2000, it expanded stores by another 31 percent.29 And then things took a turn. That year, sales fell, and then kept falling. Mickey, too, fell from grace

Forces far bigger than Mickey were churning on the horizon. We tend to think of “fast fashion” as a phenomenon of the late aughts, but when the Swedes of H&M landed on American soil in 2000, hawking $19 facsimiles of dresses that had just stalked the runways

the economy had weakened in 2000, and would fall into a full recession in the aftermath of 9/11

almost two decades later, uniformity and sameness were starting to look a little . . . same-y

Gap needed to shift gears, differentiate itself from its competitors and its own offshoot, Old Navy

So he tried it; for a few seasons, Gap swerved into trends. This was a huge mistake

No. The real problem, increasingly apparent in years to come, was that Gap Inc. was extravagantly bloated

Later, Mickey would call Gap’s drastic expansion the biggest mistake of his career, claiming that—though he oversaw the growth—he was opposed to it.

Mickey’s style of micromanagement was not suited to the sprawling corporation The Gap had become. Deep down, Mickey knew this.

(Paul Pressler, who would be tapped to replace Mickey, came from Disney.)

Jobs was a born rabble-rouser whose unfiltered opinions had a way of shaking up everyone else on the Gap board, which largely consisted of Fisher’s allies. That night, Jobs was once again going off script. “You’re going to get fired tomorrow,” he told Mickey

For four months, to Fisher’s amazement, Mickey worked harder than ever, determined to turn the company around. By that fall, he believed he had set them on the right track. But the decision stuck.

Chapter 13: This Is Your Captain Speaking

As the head of womenswear, Jenna was to come in early the next morning to meet her new boss, Mickey Drexler. Jenna’s first thought was not: The merchant prince is here to save us! More along the lines of: Geezus. Another one? At thirty-four, Jenna had toiled at J.Crew for thirteen years, her entire career.*

In 2002, when Scott Formby, her mentor and the person who, for years, had been her after-hours work confidant, was finally pushed off of J.Crew’s rapidly shrinking island, Jenna was crowned head womenswear designer

Jenna and her team had now completely redesigned J.Crew—no small undertaking—not once, but three different times

Over the past six months, Ken Pilot had swung J.Crew in the direction of Banana Republic–sleek. That look didn’t feel right to Jenna, but what could she say? She was hired help. And now . . . Mickey Drexler?

MICKEY WALKED INTO J.CREW THE NEXT DAY WITH SKIN IN THE game. He was not just T.P.G.’s latest C.E.O.-for-hire, but a major shareholder, having invested $10 million of his own money for 10 percent of the company

On paper, J.Crew was a shocking demotion for the merchant prince. By 2003, sales had dwindled to $766 million—about one-twentieth Gap’s.4 Mickey found a way to spin that as a positive. He had learned his lesson: “I don’t do big well,”

On day one, Jenna walked out of that first early-morning meeting with Mickey to find workers already stringing wire for a new office-wide intercom system. This way, Mickey could speak to the entire company at the press of a button. “I was like: are you kidding me with this?”

he was impatient. He didn’t know who these people were or what each of them did, and he had nonstop questions, ideas, and demands. No way was he going to leave a message on someone’s voicemail and wait for the answer to trickle up

Step one: “Get rid of the ugly.” Or, to use another Mickey-ism, cut the “schlock.”

On day two or three, he gathered every style J.Crew currently stocked, plus all the samples of what was on order for the upcoming season, plus much of the company staff in one room.7 The employees would present the goods, item by item

announced, “You’re all interviewing for your jobs.”

What happened next has become the Cinderella story of Jenna, a woman who emerged from the nameless, faceless ranks of mass retail—from the unglamorous bowels of a catalogue company, no less: unheard-of!—to become a bona fide fashion star.

She took a deep breath, and let ’er rip: only one of the three was worth keeping, she said. Mickey did not flinch. “Fine,” he said, “throw the others on the floor.”

“I was so confused, and I was scared, but I was also a little bit excited, because all the things that I liked and I thought were brand-right, he was leaving up on the wall,”

Jenna also didn’t know that Mickey had already been tipped off by Todd Snyder, his trusted menswear designer at Old Navy, to look out for this woman, Jenna Lyons. Now, in Mickey’s gut, a familiar excitement was building: the thrill of locking in on a core member of his future team. To Mickey, identifying people who had the right ideas, the right temperament, to take a company forward—his people—was more memorable than adding another industry trophy to his pile

As far as Mickey was concerned, this company was a shitshow. But he knew there was something worth salvaging here, a nugget of gold buried deep in the mess: the brand itself

Unlike his “get the red out” siege at Gap, Mickey was not out to eradicate J.Crew’s past. If anything, he wanted to rewind the tape back to the feeling the brand once conjured

Mickey gave Jenna the green light: “Okay, get on a plane. Go to Hong Kong, start developing new product, and re-present

“Why is the whole place on sale?” he crowed in meetings.

bankruptcy loomed. How were they supposed to keep the company afloat and cut the things that still made money?

When Mickey learned that J.Crew clothes were being sold through third-party retailers—other, not-so-hot websites—his orders were unequivocal: “Kill it. I want the entire thing dead right now.” But those affiliate sites accounted for 10 percent of all online sales.

Chapter 14: Panning for Gold

cashmere was having a moment—still a staple of the rich, but also proudly sported by the not-so-rich year-round, in every ply, weight, and hue. Mickey wanted to sprinkle some of that fairy dust over his beleaguered brand*

someone was getting fired every week. The pressure was “bone crushing,” one Mickey veteran told me, and the office politics were dog-eat-dog: factions were forming, and Mickey seemed to enjoy it

At other retailers, C.E.O.s were being hired to pore over data and spreadsheets, but at J.Crew it worked somewhat in reverse. Mickey largely trusted his deputies to stay on top of the number crunching. The nitty-gritty of customer relations was Mickey’s job, perhaps his greatest skill

It seemed to finally dawn on Mickey: these people were too paralyzed, too fearful of him, and whatever he was about to do next, to catch the adrenaline jolt he was trying to transmit. In the Cinader era, silence had been required, and prized. With Mickey, silence simply never occurred. There was no “low” on his dial. He processed externally*

Showmen do not like a dead audience. As Valdivia tells it, Mickey took matters into his own hands. The merchant prince, age fifty-six, climbed up on the table, lay down, and began to drape himself in sweaters, rolling around like he was bathing in knitwear*

But at last, the tension was broken. A few people started to laugh. That moment “was a huge unlock for everyone,”

The first was that part of their jobs—perhaps the most critical part—was going to be keeping Mickey himself excited, engaged, entertained. The second was that anyone who cared this deeply about cashmere, of all things, was not planning to turn J.Crew into wall-to-wall tees and khakis. The relief was palpable

all of it was leading to a place that J.Crew, despite appearances to the contrary, had never actually been—true, unadulterated prep

But this time around, prep came with a new accessory: a wink

Early on he asked Valdivia to design a window for the Fifth Avenue store that telegraphed a message any passerby would absorb with a single glance

Finally, he hit Mickey’s sweet spot. He proposed a line of mannequins in collegiate navy blazers and Nantucket-ready “critter pants”—the same cutesy embroidered lobsters, whales, and anchors that Emily had loathed—in front of a bright blue backdrop that read, Catch a critter! He even blew up oversize images of these critters, that looked like they were scurrying across the background.

Catch a critter! was as succinct as Miles Davis wore khakis

It didn’t hurt that the Fifth Avenue store, where those windows debuted, was right across the street from Gap’s New York offices

CASHMERE WAS HIS FIRST REALLY BIG SWING. TWO OF MICKEY’S earliest questions for Jenna had been “What’s wrong with our cashmere? Why are our colors so dull?”

for years, Loro Piana had also sold cashmere to J.Crew. Scott Formby and Arnie Cohen had flown to Quarona to negotiate a deal back in 1989. But then in the T.P.G. years, rarefied yarns became a relic of J.Crew past. Within months of Mickey’s arrival, despite its budgetary crisis, J.Crew was again investing in Loro Piana cashmere—and selling curiously soft cashmere crewnecks*

One clue as to how they managed to pull this off: These yarns may have been spun in Italy, but from there they took a sharp left to the Far East, where they were stitched together. The cashmere was from Italy. The sweater was from Hong Kong

The deal had always been that J.Crew could sell Loro Piana, as long as they didn’t tell anybody it was Loro Piana

He had installed a full-scale PR and marketing department, something Emily once actively spurned, which would soon extol other rarefied suppliers

put J.Crew’s new-sounding (if not wholly new) mantra, “affordable luxury,” on the map

They were all in awe of Mickey’s legendary gut. “He could look at an assortment on a wall and pick the home runs,” Todd Snyder recalls. And when Mickey saw a winner, he didn’t just buy 10 percent more of it—he bought twice as many

What he was not doing was the day-in, day-out focused work of keeping a company on track

“What really changed the trajectory was when he hired Tracy Gardner,” says Snyder. “In my opinion, she was the secret sauce.”

Gardner had worked with Mickey at Gap Inc. since she was twenty-five, most recently running the Gap brand

Gardner was experienced in managing Mickey. As Snyder puts it, “She wouldn’t overlisten to Mickey.”

In addition to Jenna, Snyder, and new head of marketing and PR Margot Fooshee, Mickey’s coven included Jeff Pfeifle, the former head of Old Navy; Jennifer Foyle, the master merchant with a sixth sense for what customers would love; operations expert Valerie Vanogtrop; and Jen Myerberg, a savant of distribution

erecting what was really a new company—product by product, catalogue by catalogue, store by store. It bore the name and some of the genetic material of the original J.Crew, but under the hood, the engine was all Gap

They knew how to turn Mickey’s rapid-fire brain waves into full-fledged businesses

Chapter 15: Redemption Day

June 28, 2006. The dual redemption of J.Crew and Mickey Drexler was official. That morning, standing on a podium just above the melee of the New York Stock Exchange, looking unusually corporate in a wide-stripe rep tie and navy jacket, Mickey rang the fabled bell

Even as they stood there, though, this I.P.O. was far from a sure bet. Mickey’s turnaround had been dramatic, but its track record of success was brief: The company had shown a profit for the first time in ages just one year earlier, in 2005. The J.Crew they took public was heavily leveraged, strapped with $590 million in debt—twenty-four times its $25 million in cash

Now that J.Crew had made it to the I.P.O., Emily—still a board member and part owner, and now at least $100 million richer herself—could make a clean break. Which she did, six months after the I.P.O

the place where Mickey had always found growth before—the mall—was becoming an increasingly risky bet

If growth couldn’t come from footprint, it had to come from demand

J.Crew’s former niche as America’s classic, pared-down, upscale outfitter for office and weekend? Zzzzz. Minimalism felt boring, suburban, the same. And shopping itself had changed: high-priced fashion was going ever higher; low-priced fashion, ever lower. Mickey spied a “white space” J.Crew could occupy, nestled between designer and mass.

Zara alone was a rather terrifying force: Everything about this company was an existential threat to any specialty retailer like J.Crew, which designed its clothes a year in advance

authenticity was all about rough edges

Mickey had one in his back pocket. If J.Crew wasn’t opening a fleet of new stores, it was expanding—and keeping shareholders happy—by following the gold-plated example of Old Navy: launching an offshoot


The first Madewell store opened on lower Broadway, in Soho, in 2006

JENNA LYONS COULD BE A SWEETHEART, A CHARMER, QUICK WITH a joke, always self-deprecating. But she was not a pushover. And she could see that the era of “authenticity” had wiped out fashion’s brief dalliance with prep

It wasn’t that Jenna hated prep, exactly. But her idea of an argyle sweater didn’t come with trousers, loafers, and a beret. A Jenna argyle was exploded into an oversize pattern and paired with camo pants

Jenna had a set of uncanny, almost Carnac-like abilities all her own. She could walk into any store, see a mishmash of good, bad, and weird, and know exactly what to eliminate to bring the whole thing into focus

it hit Mickey all at once, a true light bulb moment: “Wait,” he said. “You’re the coolest-looking woman ever. Why aren’t you just doing you?”

Chapter 16: The Tao of Jenna

Jenna’s memory holds no black-and-white “you do you” Mickey moment. In her mind, the transition wasn’t that clean

Just as Emily had built J.Crew up around her, an extension of her tastes, her history, her worldview, now Jenna was making it her own. And the first rule of Jenna’s world was that anything too “correct,” too “perfect,” felt wrong

Most people at J.Crew back in the ’90s would never have guessed Jenna would become Jenna. She was talented, but then weren’t they all? But at least one thing about her was notably different from the rest. “We all liked fashion,” recalls a designer who worked closely with her back then. “Jenna was more amped up about it.” On inspiration-shopping excursions in Europe, Jenna wasn’t just buying samples for J.Crew inspiration. She shopped for herself

TOGETHER, JENNA AND GAYLE SPANNAUS TURNED J.CREW’S CATALOGUE styling area, aka the “styling cage,” into their laboratory

For Jenna and Spannaus, the question in their heads was never “What is the J.Crew woman going to like?” but rather “What do we like?”

what they were making was very much a product of its time

designers had skipped the long slog of working one’s way up in a storied maison or at some Seventh Avenue powerhouse, and instead opened their own labels, sometimes straight out of design school. “Young designer” was a retail category now

No one had found a way to market “personal style” to the masses. Yet.

Her dressed-up/dressed-down ethos echoed “the Eastern Establishment virtues of being dressed down from a formal perspective, and dressed up from a casual one,” as Ivy Style founder Christian Chensvold put it.11 Wabi sabi. Sprezzatura. The hint of imperfection—even if it’s a carefully crafted illusion—that makes it cool.

She was working on the company’s first lookbook. This in itself was a turning point: Lookbooks are like mini-catalogues, made specifically for the fashion editors and stylists

Chapter 17: Mad Men and Brooklyn Loggers

breakfasts with Roger Markfield

Markfield, then C.E.O. of American Eagle

Markfield bragged, “I told Mickey, ‘It’s all shit. Don’t kid yourself—there’s no value in anything you’ve got hanging on those racks.’ I really let him have it.

it suddenly became more acceptable for ‘normal’ guys to be interested in their appearance

traditionally masculine—handy! hairy!—but also evolved

“I had breakfast with Roger,” he told menswear designer Todd Snyder. “He thinks we’re too ‘dandy.’ We need to pivot.” In Snyder’s recollection, “Mickey turned on a dime.”

many a late night at Freemans, the downtown restaurant that was the new unofficial HQ of the lumbersexual

its enviably cool waitstaff exemplified the look of the moment: turn-of-the-century mustachios, navy watch caps, deep-cuffed raw denim, scuffed Alden boots

The revamped J.Crew menswear was among the first brands Michael Williams ever covered on ACL. In Williams’s view, J.Crew packaged the look “better than anyone,”

He wanted to stock Red Wing boots, at a Red Wing price, in J.Crew stores

How do you get skeptical guys to trust your clothing? You pair them with things they already trust

Red Wing made boots for hunters and log splitters that cost upward of $300. How much log splitting was J.Crew’s mall-shopping prepster really doing?

Mickey thought the idea was worth a shot. The other J.Crew merchants played along “just to shut the designers up,” Snyder says with a laugh. The first order was tiny: one hundred pairs. Those blew out within a week

Next came Timex watches; then New Balance sneakers—Mickey wore them constantly; then tailored shirts by the English firm Thomas Mason

These guest stars came to be known as “In Good Company” collaborations. It mostly wasn’t about profit

what was the point of having an amazing new look without a proper boutique where it could all come together

Spade took Mickey and Todd Snyder on a field trip. He knew the perfect spot: a tiny, grimy out-of-work bar on a crooked corner in Tribeca. The original bar was still intact, down to the bourbon bottles, and the little neon sign in the window: Liquor Store

In the back of the store, there would be a separate room for suits. Really, a suit.

It took Snyder and Frank Muytjens two years to tweak the Ludlow Suit to perfection.

“I’ve never seen a suit that fits so many body types off the rack.”

The Liquor Store never made a ton of money, but that wasn’t the point. It put J.Crew menswear on the fashion map. And provided a gold mine of data.

Chapter 18: The J in J.Crew

watching The Tonight Show, when she gasped and jolted up. “I almost took his eye out,” she recalls. Michelle Obama had just walked onto the set. “I knew instantly she was wearing head-to-toe J.Crew.”

they’d been hit by the recession at a vulnerable moment

Who could give J.Crew a believable—even lovable—personality?

They had just the woman. By late ’08, Jenna was president and creative director of J.Crew, reportedly with a signing bonus of $2 million and a base salary of $675,000.

The last time “the” American brand was anointed, all praise had been directed at Mickey. This time the spotlight swerved in a different direction: directly onto Jenna Lyons.

J.Crew had wanted a celebrity designer. What they got was a full-blown celebrity

But from what her colleagues could tell, Jenna loved it. “She became her own creation,” says a colleague. “And she wanted it badly

Chapter 19: Everyone’s an Expert

Just as Jenna shot into the stratosphere, word around the J.Crew offices was, Have you heard about this guy, the Sartorialist?

She restructured the creative side of the company, pooling the teams for the various divisions

It put everyone on the same page

“it felt like we all had the same point of view,”

In marketingspeak, they needed “emotional coherence.”3 Walk into any Apple store

Not only did she oversee all the big things—store interiors, web design, perfectly layered catalogue looks—but also, to an almost impractical degree, she saw the little stuff, too. Every last email blast to the customers required Jenna’s sign-off

They needed more than a vague sense of authenticity; they needed “personality,” voice. Content! A website stuffed with articles that had nothing to do with the stuff they made, to wrap the hard sell inside a fuzzy blanket of storytelling.

A former Domino editor was hired to develop the voice of the new Style Guide, aka the catalogue, which had a new kind of heavy lifting to do—now that it was an instruction manual to the J.Crew life

brand fans are different. J.Crew Aficionadas loved J.Crew, but they also expected more from it. T

Chapter 20: Let’s Make a Deal

In the downturn, J.Crew had appeared to be headed for the gutter along with everybody else, but in 2009, they shot right back up to the surface: profits jumped 40 percent

In the summer of 2010, Tracy Gardner told Mickey she was stepping down

some of the higher-ups were already starting to fret: were they trying to be a fashion brand now? In an almost uncanny repeat of the Emily era, the business team was side-eyeing J.Crew Collection all over again.

As early as 2009—just as the Mickey-Jenna era was hitting its cultural peak—key merchants from that ex-Gap team saw the prices edging up, and the clothes getting trendier, and worried

He pulled Jenna into a room and informed her, with little preamble: “Just want to let you know you’re the president.”6 Not just of J.Crew, but of the whole company

what if the two firms bought J.Crew, took it private, stoked its fires, and eventually went public all over again—for even more money?

Mickey would later frame his role in this scenario as that of innocent bystander

and he worried from the jump that a new LBO would saddle J.Crew with a crippling amount of debt. (Which was exactly what happened.) That’s a very different version of the story from the one that was widely reported in the press, and from the way the deal was perceived on Wall Street and, indeed, by many of Mickey’s own employees. This second-time-around LBO, as far as most people were concerned, was Mickey Drexler’s baby

This time, the upside for J.Crew, the company, was less evident

Eventually, these shenanigans landed Mickey and Co. in court. Shareholders balked at the short notice, not to mention Mickey’s cozy relationship with Coulter

Chapter 21: Page Six on Line One

They’d just gotten a call from the New York Post. “They’re running a story that you’re seeing a woman. Should we confirm or deny?

Chapter 22: Cognitive Dissonance, Part Deux

the brand had caught the eye of one of the richest men in Japan.2 Tadashi Yanai had admired Mickey since the ’80s, when he studied the Gap’s winning formula as a model for his own company, Uniqlo*

Yanai was said to be insulted by the bloated price tag. Talks of a buyout died there.

inside the company, a crisis was brewing. One that J.Crew had plenty of time to see coming.

with success had come a new overlord: comps. Retailspeak for a store’s current sales, compared to those of the previous year.

Now, every time J.Crew staffers walked out of 770 Broadway, they saw the windows of the nearby Ann Taylor plastered with eerily familiar, blown-up photos

Copycats are all part of the game

J.Crew needed an answer to that question: What’s next? But no one seemed to have one

What happened next? You guessed it. A pendulum swing.

Suddenly, ease was the thing

Just as comfort footwear was trickling down from the runways of Paris, something not totally unrelated was bubbling up from the streets. The kids were calling it “normcore.”

the J.Crew of the 2010s had bet the farm on special

Hang on, what was happening here? A $1,000 furry slipper from Paris, plus a trend so niche that the suburban dads whose closets it borrowed from have likely still never heard of it—these things had thrown a curveball at the mighty J.Crew? Absurd

by the 2010s, the trend cycle turned on a dime, spinning faster than ever

These chains had changed consumer psychology: they retrained us to expect constant novelty

Why hadn’t J.Crew just stayed in its lane, sticking with basics?

It was the result of consumer research, which kept telling them: Special. Festive. New. Fun. That was what women expected of J.Crew.

In her 2013 fast fashion exposé, Overdressed, Elizabeth Cline—the Michael Pollan of the fashion industry—traces the start of the fast fashion mentality back to a curious source: one Millard “Mickey” Drexler.7 Cline argues that Mickey’s Gap was the O.G. fast fashion retailer, the first to convince shoppers—through a flood of high-end ads and high-profile appearances by, say, Sharon Stone—that low-price clothes were a viable alternative to higher-end fashion.

But they still kept pumping those necklaces into catalogues and stores and the website

They had sold a boatload of bubble necklaces last year, so they’d invested heavily in bubble necklaces for this year. That investment was made two full fashion seasons before the necklaces would hit stores.

Jenna’s team tried to pivot, veering from kooky to classic. They put out a catalogue awash in elegant grays and camels, dialed back almost to Emily-era minimalism. It flopped

now almost every phone in the U.S. was a Wi-Fi equipped smartphone. People squinting at some four inches of screen couldn’t see a lot of what J.Crew promised: the artful construction details and Italian silk were lost on a new consumer, who likely didn’t care anyway. The younger customer “doesn’t want to read an entire fucking essay about how their sweater got its name,” says a copywriter. “She doesn’t have the attention span for that.”

In late 2011, Bain & Company retail consultant Darrell Rigby published a paper in the Harvard Business Review detailing the “start-from-scratch, across-the-board innovation” retailers urgently needed to undertake, not to thrive in the future of shopping, necessarily, but just to survive to see it

In some ways, this didn’t describe J.Crew at all: Mickey’s iPhone was surgically attached to his hand

But if any of his employees had read this report, they might have seen other red flags. In website review meetings, it was clear Mickey wasn’t used to navigating J.Crew’s own site. Just as Arthur and Emily had once been catalogue people, Mickey was fundamentally a shopkeeper—forever stalking his stores, quizzing customers, answering their kvetching emails in the wee hours. The online world largely left him cold. In this, he was very much the type Rigby described.

J.Crew had a killer website

by 2014, the site was only one piece of the digital puzzle. Facebook, Instagram, Twitter, Google, YouTube, Snapchat: each required a custom approach; each had a slightly different audience

Social media had moved the goal posts of “authenticity” yet again

So though they did hire an in-house “social” team, they produced their feeds as carefully as catalogue pages, complete with location scouts and casting agents

Now, preached Darrell Rigby, was the time for retail C.E.O.s to achieve “perfect integration of the digital and the physical.”

The company infrastructure was inefficient, dated. Customers still waited a week to get the shorts they needed for vacation and they still paid for shipping

Meanwhile, a new kind of competitor had arrived on the scene

These were digital natives, “disruptors”—Bonobos, Everlane, Reformation, Warby Parker

They were unencumbered by long store leases

Stitch Fix (Stupid company)

Bonobos, the menswear startup, had poached a series of designers from J.Crew’s team.

Whatever the reason, when Fast Company landed on newsstands across Manhattan, some believed Mickey was less than thrilled

As far as the staffer I spoke with was concerned, it was clear that Mickey’s problem with Fast Company was really a problem with Jenna

IT WAS NOT UNTIL DECEMBER 2014 THAT J.CREW’S DUAL identity—glowing success in public, increasing cause for worry in private—was made public

plunged, in a single year, from a net income of more than $35 million to a loss of nearly $608 million.15 Plans for a second I.P.O. were shelved

The women’s business had plummeted

Chapter 23: Knives Out

In 2015, there was no denying it: the God of Retail Pricing had smote J.Crew.

The company was up against all the things that were ailing every other retailer of their ilk

So much of what J.Crew was up against was big and global. But many of its wounds were self-inflicted.

Take pricing

He just kept pushing it north,” she says. “He so believed in the novelty and the appeal of the clothes

Today, both Mickey and Jenna maintain the problem wasn’t higher prices, but something more insidious: the perception of higher prices

the fancy stuff hogged the spotlight, overshadowing the workaday basics. It made people think J.Crew was more expensive than it really was

a nod from Vogue isn’t always a good thing for a company like J.Crew. If the magazine ran a photo of a $400 sweater, “the perception is Oh Jesus, J.Crew sweaters cost $400?” he says. “That alienates more people than it attracts.”

doesn’t give those customers a lot of credit. Especially since prices did inch up.*

He has to be surrounded by people who can do it with him. There’s always a right group of people.” But by 2015, who was playing that role in Mickey’s inner circle?*

it, “He doesn’t ask a question he doesn’t already know the answer to.”


A veritable Greek chorus had been wailing about all of this—price, fit, quality—unheeded, for years. “J.Crew should be reading this blog,” one J.Crew Aficionada commenter wrote, “if they knew what was good for them

Now, JCAs were getting what they wanted, in one respect at least: after revenue dropped in 2014, the discounts Mickey had railed against so vociferously in his early days—“pull out the needle!”—became a permanent feature. Twenty percent off became 40, became 60

IN MARCH 2015, OREGON-BASED ARTIST TRICIA LOUVAR SUBMITTED an illustration to the feminist website The Hairpin. She called it, “An Open Letter to Jenna Lyons”:2 Dear Jenna, You are pretty dope . . . If only I, an ordinary mother on a modest income, could afford to wear a $400 cashmere skirt*

It was all part of a massive tide that was beginning to turn: consumers were speaking truth to power, questioning both the corporations and the image-making machines that had long told them how they were supposed to look, act, and think

In the clothing realm, a lot of these conversations were kicked off when people started questioning size ranges.

other companies seemed to be paying increasing attention to women’s actual lives and habits: Lululemon, Ann Taylor, and Old Navy had jumped on this new thing, athleisure, which accommodated both their gig-economy jobs and a wide range of bodies

67 percent of American women could not shop J.Crew clothing at all because they were a size 14 or larger.5

For years, the company had catered to two different bases, like a purple state politician: fashion people and “real” people. Now, instead of hovering in a sweet spot between the two, the covetable “white space” they had conquered felt more like a no-man’s-land middle

Working women, prepsters, Basic Bettys, we were the J.Crew market base. We wanted good quality staples at a fair price with the occasional bit of flair

June 15, 2015

J.Crew’s woes were no secret: same-store sales were down 10 percent from a year earlier

EBITDA had sunk 31 percent from the same period in 2014

The Times’ fashion pages might have been blaming Jenna for J.Crew’s problems but in its business pages, columnist Steven Davidoff Solomon went after Mickey. J.Crew had a “‘Great Man’ dilemma,” Solomon wrote, that was specific to the merchant prince.10 If Mickey hadn’t been Mr. Gap, then Mr. Old Navy, and now Mr. J.Crew, no one would have followed him down the garden path of 2011’s messy $3 billion sale. That deal had only gone through because he was the Mickey Drexler. So, no, J.Crew’s crippling problem was not sweaters. It was something Mickey had not elaborated on during that earnings call: $1.5 billion in debt

J.Crew was paying T.P.G. and Leonard Green at least $2 million per quarter in consulting and management fees. Between 2011 and 2015, that reportedly tallied $685 million in dividends to the two firms, and $55 million to Mickey himself, so far, for his stake.

Chapter 24: Three Horsewomen and an Apocalypse

In April 2017, a month after the latest round of layoffs, Jenna was on a much-needed beach vacation when someone overheard her talking about a plan to exit J.Crew. This made it to a reporter, who called J.Crew for comment. Many believed the designer was planning a more gradual exit down the line. But the leak fast-fowarded her timeline

May 2, 2016. The steps of the Metropolitan Museum of Art

Jenna Lyons towers over Lena Dunham and Jenni Konner. With her arms draped around their shoulders in jokey hauteur, she perches over them like a very chic praying mantis. The matching outfits had been Dunham’s idea*

Many at J.Crew say Jenna was working harder than ever to fix their problems. Others thought she was checked out

“We got a little bit full of ourselves,” said a J.Crew V.P. “You know, we weren’t high fashion—we obviously weren’t Phillip Lim, or Céline. But we weren’t the Gap.” Now the reality check was harsh: “We were,” she said, still a little stunned. “We were the Gap.”

It was an eerie repeat of the early T.P.G. years. In came the analytics, the roving bands of consultants trying to plug the leaks and find what’s broken

A new phrase crept into their conversations: who is our girl? It was a depressing question, one they had not needed to ask for at least twelve years


At the same time, there was an inflection point in online shopping. According to a Pew survey, in 2017 Americans were “starting to shop online as often as [they] take out the trash

Among the paradoxes of Mickey

is the fact that he could not have missed that this was coming. Mickey had a front row seat to the digital revolution, sitting on the board of Apple for sixteen years.

“We talked about it, for sure, and it was moving in this direction,” Mickey said. “But the speed of it—I wasn’t prepared for it.”

IN FEBRUARY 2017, J.CREW SEEMED TO DEMONSTRATE THAT IT had, in fact, been listening to its customers’ complaints

they were back to rugbies and rollnecks, plus some greatest hits from the Jenna years

Mickey genuinely believed in this reinvention

he had a lot of faith in the talent of their new head of womenswear, the J.Crew/Madewell vet Somsack Sikhounmuong

Jenna says that making decisions about J.Crew “used to feel really innate—like I knew exactly what I wanted, was charged to push through.” But her foolproof sense of what was and wasn’t J.Crew had started to fail her

It began to feel as if Jenna had stopped pushing back on the merchant side

She’d been at J.Crew twenty-six years—eight years longer than Emily herself

In the first six months of 2017, Payless, Limited, BCBG Max Azaria, and Wet Seal all declared bankruptcy

Yet none of the C.E.O.s of these companies were taking heat quite the way Mickey Drexler was

“Mickey needs, but does not want, someone to put up guardrails,” says retail analyst Richard Jaffe. Everybody knew Mickey didn’t like having a boss—he’d said so himself. But by now it was clear to most that he needed one—or at least a powerful counterweight

“Mickey and Jenna enabled each other,” says a designer

By the early summer of 2017, the comparisons to Gap were inevitable: J.Crew had been down eleven of the last twelve quarters. It wasn’t enough for Jenna to leave. Mickey had to go, too

He was able to have a hand in picking his successor. But every person he interviewed, he rejected

Finally, the headhunter sent in James Brett. As president of the interiors company West Elm, Brett had led twenty-four consecutive quarters of double-digit revenue growth

No. Not this guy, Mickey told Jon Sokoloff and Jim Coulter. He’s going to bankrupt the company. This time, he was overruled. Brett was in.

Chapter 25: The Cherry Pickers

Jim Brett’s tenure was as disastrous as Mickey predicted.

Almost all of Brett’s changes went live in one high-speed stretch in September 2018. Two months later, he was out after seventeen months.

His successor, Jan Singer, lasted less than ten.

Then came March 2020, and the most devastating global pandemic in one hundred years

Less than six weeks into the lockdown, J.Crew filed for Chapter 11 bankruptcy protection

two married lawyers, Mark and Patricia McCloskey, made headlines for standing in front of their St. Louis manse wielding guns at peaceful Black Lives Matter protestors

the first thing anybody saw was his giant black AR-15 style rifle. But the second thing you noticed was their clothes. Patricia wore a bateau-striped T-shirt. Mark had on a pink Brooks Brothers polo and light khaki pants. They looked like the embodiment of the establishment

Cintra Wilson, writing for Town & Country, said the McCloskeys had unwittingly pulled Brooks Brothers, “a 202-year-old symbol of American normcore, into a national polemic.” It was now “the label of the un-woke.”

The Future of Shopping had not turned out quite as expected. Between 2019 and 2021, online shopping spiked by more than 50 percent—no great surprise, since it had been headed in that direction, even before America got locked inside on our laptops.8 What was surprising was that many of retail’s digital wunderkinds, the upstarts who appeared to be sure bets at the end of the Mickey and Jenna era, had failed to deliver, so to speak. As of this writing, the clothing rental service Rent the Runway reportedly had “a long road ahead to profitability,” with a net loss of $211.8 million in 2021.9 Investors were likewise losing patience with secondhand giants the RealReal, Poshmark, and ThredUp, which all went public in splashy I.P.O.s—and all have yet to turn a profit.10

What did seem to be working? Real-life, in-person stores

But the most curious about-face of the late-pandemic era is also maybe the most inevitable: “Preppy style is back with a vengeance!” shrieked the Guardian

J.Crew emerged from Chapter 11 with a new majority shareholder, New York–based hedge fund Anchorage Capital Partners, and a new, lighter debt load of $400 million, not due until 2027

The second, most obvious sign of hope: new design talent

Brendon Babenzien, who spent almost fifteen years as the creative director of Supreme, arguably the most influential streetwear company of all time

I can’t imagine how any single retailer could ever be the American brand again

J.Crew doesn’t need to be that again to be indispensable again. What it needs are those fleeting moments when it makes us believe, when it makes us think, “This! This is what I want my life to look like.” (Fucking sad)

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