J. Crew and the Paradoxes of Prep

By mass-marketing social aspiration, the brand toed the line between exclusivity and accessibility—and established prep as America’s visual vernacular.
A collage of preppy people in photos mixed with sewing materials.
Where traditional catalogues highlighted the product, J. Crew emphasized scenes, tableaux, glimpses of leisurely cool.Illustration by Nada Hayek

Duck boots, barn coats, and turtleneck sweaters seemed deeply eccentric in the sunny, laid-back suburb of Silicon Valley where I grew up, in the eighties and nineties. These garments—among the talismanic offerings of the J. Crew catalogue that somehow appeared in the mailbox—might as well have been for wearing on Mars, and my friends and I, many of us the children of immigrants, were only dimly aware of the heritage that they were inviting us to access. (I had no idea that a person could be called a Wasp, other than the Wasp in my comic books.) But we knew that J. Crew was, enticingly, just out of our reach. And, because these clothes communicated in an insider’s code, lacking the self-identifying mark of a little swoosh or a tiny guy on a horse, they seemed mysterious, too.

I picked out the most unusual item I could find: an unlined, plaid zip-up jacket. When it arrived, it clashed with my middle-school wardrobe, a mix of basketball sneakers, my father’s old corduroys, and skate-themed T-shirts. I didn’t understand that my new jacket was something one might wear to go boating, or even that people went boating for fun. Yet I delighted in wearing it along with my normal clothes, creating a garish mishmash of stolen subcultural valor. The look was awful, and it was mine.

It was also, in part, Arthur Cinader’s. When Cinader started J. Crew, as a mail-order retailer, in 1983, he was targeting shoppers who wanted something more stylish than other mail-order brands, such as L. L. Bean or Lands’ End, and more affordable than Ralph Lauren. But, where traditional catalogues highlighted the product, J. Crew’s emphasized scenes, tableaux, glimpses of leisurely cool. The pages featured the upper crust at play, horsing around and lounging about, untroubled yet serious. These were poses and postures to be studied and adopted, and here were the anoraks, chambray shirts, or roll-neck sweaters to wear while doing so. Soon after the first J. Crew catalogues were sent out, telephone operators struggled to keep up with all the calls. “You looked at the catalogue and thought, ‘I want to live like that,’ ” the designer Peter Som explained.

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Within half a dozen years, the brand had become synonymous with preppy apparel, and Cinader decided to open its first brick-and-mortar shop—a potentially risky move for a business based on a meticulously conceived catalogue. But he and his colleagues enlisted catalogue data to make decisions about location. The first J. Crew store was in Manhattan’s South Street Seaport, a tourist zone that also happened to be close enough to Wall Street to catch the after-work crowd. The night of the grand opening, a fire marshal was said to have shown up because of reports of overcrowding. When J. Crew expanded to Boston, Cinader and his colleagues targeted the Chestnut Hill Mall, an accessible distance to at least a dozen colleges. “We never meet a college student who doesn’t know J. Crew very well,” Cinader said. By the mid-nineties, J. Crew, still a family-run business, was opening stores across the country and sending out seventy million catalogues a year. More important, it was permeating culture—competitors imitated its catalogues, and, where it had once positioned itself as an affordable alternative to Ralph Lauren, upstart brands now offered themselves as down-market alternatives to J. Crew.

All of them were trying to replicate the potent yet amorphous sensibility that had captivated Cinader: prep, which the author Maggie Bullock describes as “the bedrock of straightforward, unfettered, ‘American’ style.” Her new book, “The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J. Crew” (HarperCollins), is a buoyant and persuasive account of how the company’s fluctuating fortunes reflect Americans’ shifting attitudes toward dress, shopping, and identity.

At the center of Bullock’s story is the malleability of prep, which she depicts as the “leisure uniform of the establishment.” What people consider to be cool changes with time, but coolness always presumes exclusivity and effortlessness. At its height, Bullock argues, J. Crew embodied the nonchalant, “broken-in cool” that typified prep. What’s complicated about the mass-marketing of social aspiration, though, is that it’s more about belonging to a group than about standing out as an individual. The class fantasy at the heart of prep style was the prep school, where dress codes offered a way of diminishing the differences among its students. This was a different temperature of cool from, say, the leather jacket. With the rise of prep fashion, you could dress up like members of the ruling class, even if the looks you mimicked were solely of them dressing down.

“Prep” didn’t start out as an aspirational identity. The term gained wide currency with “Love Story,” the 1970 blockbuster film about a working-class Radcliffe student (Ali MacGraw), who falls in love with a Harvard blue blood (Ryan O’Neal). She calls him a “preppy” to tease him, but eventually it becomes a term of affection. For many, the expression brought into focus an entire history of Northeastern prep-school privilege, a style associated with Wasp culture. In 1980, Lisa Birnbach’s “The Official Preppy Handbook” was published, as a tongue-in-cheek guide to the fashions, speech patterns, and codes of high society. It was satire, but no offense was taken. As Bullock writes, “Rich kids love poking fun at their own privilege, so long as they don’t lose any of it in the process.” And, for those who aspired to join their ranks, the best-selling book offered a script for acting the part.

Prep fashion has its roots in the nineteenth century. In 1849, Brooks Brothers introduced the ready-to-wear suit to American consumers, radically changing how people dressed. The availability of premade garments in standardized sizes had two effects: it made “gentlemanly” dress affordable to everyday workers, and it loosened the silhouette of menswear from the fitted, custom tailoring of the Victorian era.

Bullock argues that Brooks Brothers’ roots could be construed as “deeply egalitarian”—the firm sought to outfit the common worker. Yet by the early twentieth century its clothing had become identified with élite boarding schools and the Ivy League institutions that they fed. In F. Scott Fitzgerald’s “This Side of Paradise,” partly set at Princeton during the nineteen-tens, the undergraduate poet Tom D’Invilliers laments how dress became a competition, with his classmates keenly attentive to details like “the color of their neckties and the roll of their coats.” Even during the Great Depression, Ivy League campuses were a laboratory for leisure-wear experimentation: penny loafers and bucks, varsity sweaters, banded V-neck sweaters, all assembled with the nonchalance of true Wasp privilege. “Nothing identified an outsider like a too-crisp collar or a spit-shined brogue,” Bullock writes. “A man who confidently strolled into class or an office in well-scuffed bucks didn’t have to worry he’d be held back by some bourgeois triviality. He knew where he stood. So did everyone else.”

Soon campuses were overwhelmed by the cohorts who arrived after the Second World War. From 1945 to 1957, 2.2 million veterans, largely from blue-collar backgrounds, enrolled in college, and they needed to dress the part. Shops such as Brooks Brothers and J. Press sold respectability, even if a few of your tonier classmates were secretly judging the color of your tie. What became known as the Ivy look—full of versatile basics like T-shirts, khakis, and sports coats—was a uniform for a society that saw itself as classless, clean-cut, and optimistic. Adopting the look was a way of fitting in at a time when society seemed open to reorientation. This appeal also held for African Americans during the civil-rights era, who appropriated the sartorial styles of a culture that sought to exclude them. Bullock notes that Martin Luther King, Jr., Malcolm X, and Louis Farrakhan all shared a fondness for Brooks Brothers suits. The fashion critic Robin Givhan describes this style of dress as “conciliatory rather than confrontational. These were not clothes for a fight but clothes for a gentlemanly—or ladylike—negotiation.”

The countercultural movements of the sixties, in turn, brought with them a celebration of the individualism that prep style, full of codes and the presumption of shared experience, has always suppressed. The personal became political, down to issues of self-presentation: the way you wore your hair or accessorized your clothes signalled a resistance to conformity. Still, even as hippies popularized beads and bare feet (a uniform of its own, inevitably), there were those who remained infatuated with the classic look of the élite. In 1965, an influential Japanese photography book, “Take Ivy,” presented campus fashion of the late fifties and early sixties, or at least an imagined, prep-forward version. (Writing in the Times about a 2010 English-language reprint, Guy Trebay noted that it showed “essentially all the stuff you’d see in a current J. Crew catalogue.”) And, in 1968, Ralph Lauren, still in his twenties, launched a full line of his menswear, Polo. Within a few years, his signature cotton Polo shirt—the one with the polo-player logo—had become a cornerstone of preppy fashion.

Perhaps because Lauren, like Cinader, was Jewish and Bronx-born, he was alert to the codes and customs that the Greenwich set took for granted. Although sometimes described as more of a stylist than a designer—he had little hands-on experience in the making of clothes—Lauren was, above all, a visionary salesman: he understood how to extract Americana out of American history. His looks alluded to outdoorsmen and boarding-school culture, American frontier myths and even the Indigenous legacies displaced in the name of those myths. The story told by a Lauren jacket—maybe the one worn by Robert Redford in “The Great Gatsby,” or maybe the one worn by Diane Keaton in “Annie Hall”—could dissolve all manner of historical contradictions in a dreamy nostalgia.

Arthur Cinader’s dream wasn’t to become the next Ralph Lauren. Although Cinader was known as a sharp dresser, he just wanted to make a mail-order catalogue, extending what had been his family’s stock-in-trade since the nineteen-forties. He settled on clothes, though it could have easily been electronic equipment. (He probably spent more time leafing through The New Criterion—he was a longtime patron of the traditionalist journal of arts and letters—than he did perusing the fashion trades.) His first thought was to name his line for Sir Edward Coke, the seventeenth-century English jurist, but “J. Crew” proved to be more versatile and evocative. “Crew” conjured images of campus oarsmen, with connotations of upper-crust leisure. That the “J.” invited associations with the Ivy League clothier J. Press didn’t hurt, either.

Cinader claimed that the original J. Crew was a men’s haberdasher in Princeton, and at first this fib was the only original thing about J. Crew. The company adopted existing designs from manufacturers but chose the colors and attached a J. Crew label, featuring the clothes alongside items from Sperry or Woolrich to suggest kinship with these respected old-line brands. The enterprise was based out of an unprepossessing family warehouse in Passaic, New Jersey, but it deftly sold a vision of leisurely roughhousing. “The heritage of J. Crew weekend clothes is 100 years of outfitting rugby, lacrosse and crew,” the first issue of the catalogue announced. “Whence their long-wearing construction. And authoritative style.” The cover showed a man and a woman each holding an oar. Cinader had been told that even successful mail-order companies started out in the red for about two and a half years; J. Crew had broken even within eighteen months.

From 1980 to 1985, mail-order industry sales grew by fifty per cent. By the end of the decade, it was estimated that Americans received 13.6 billion catalogues in the mail—fifty for every man, woman, and child. In the nineteen-nineties, though, the industry began to stagnate. J. Crew’s brick-and-mortar stores helped it weather the downturn, but the company was now competing with mall rivals, and navigating a broader cultural shift, from department stores to other brand-driven shops. What distinguished J. Crew from the Gap, Aeropostale, Banana Republic, the Limited, or Benetton was an air of exclusivity. Few of its competitors, often tentacles of the same giant corporations, were run along the idiosyncratic lines that J. Crew was.

“Just say it was a white whale, not a beluga!”
Cartoon by Jimmy Craig

Most people nowadays associate J. Crew with Mickey Drexler and Jenna Lyons, its charismatic leaders in the two-thousands. But Bullock offers Cinader and his daughter, Emily Scott, as the brand’s often overlooked, original visionaries. Although Cinader himself had no experience with rugby or crew—he attended public schools and a state college—the brand was driven by his sensibility, which those who worked with him found “esoteric, academic, exacting.” He revelled in the evocative possibilities of highfalutin language. Sweaters weren’t just green or gray, they had “great strains of crumhorn, hautbois, and sackbut.” If you recognized that these were words—and perhaps felt the impulse to look them up—you were J. Crew material.

In the nineteen-eighties, the brand’s signature pieces were casual and outdoorsy, appealing to men and women alike: striped rugby shirts, barn jackets with pinwale-cord collars, pull-over anoraks. Scott, who joined J. Crew out of college, became a key figure in further refining the company’s aesthetic. Bullock describes Scott as wanting to make a catalogue that would be comparable to a fashion magazine. J. Crew moved from Passaic to Chelsea, and it slowly cultivated a reputation for clothes that were versatile and cool, but not inaccessibly so. “The premise was to make the kinds of clothes I really wanted to wear but just couldn’t find,” Scott once said. This meant clothing that was well constructed, durable, artfully unpretentious, inspired as much by Ralph Lauren as by the European minimalism of A.P.C. and Agnès B. Once, enamored with an employee’s perfectly broken-in Chevignon Army-Navy pants, Scott asked her to take them off so she could snip a sample of the fabric for a manufacturer to replicate.

In the late nineties, Cinader and his family were beginning to feel the stress of growing J. Crew, and they sold eighty-eight per cent of the company in a leveraged buyout by the Texas Pacific Group, a private-equity firm. It was no longer a family-owned company run according to instinct, and it went through a series of managerial transitions. One C.E.O. came from the frozen-foods division of Nestlé; he outlawed the color green as something men didn’t buy. A few years later, under different stewardship, J. Crew offered a line that featured nineteen shades of the color.

The rise of Abercrombie & Fitch during this period is part of the larger story. Last year, Netflix released “White Hot: The Rise & Fall of Abercrombie & Fitch,” a documentary that explored the brand’s heyday, in the late nineteen-nineties and early two-thousands, as it courted teen-agers with a mischievous, upturned-collar version of prep. Compared with J. Crew, Abercrombie was aggressively horny; shirtless models were stationed outside its flagship stores to lure customers, and its catalogues accelerated puberty for a generation of young people. In the high-stakes game of retail brinkmanship, J. Crew classicism suddenly started to “down-trend.”

Fashion is cyclical, and though Abercrombie wasn’t a rejection of the status quo, in the style of unkempt sixties liberation, it did harness some of the loose emotions of the nineties, offering a rascally alternative to the clean-cut and conformist. “Candidly, we go after the cool kids,” Abercrombie’s mastermind, Mike Jeffries, told a reporter. “We go after the attractive all-American kid with a great attitude and a lot of friends. A lot of people don’t belong [in our clothes], and they can’t belong. Are we exclusionary? Absolutely.” What was unusual was not so much Jeffries’s attitude as his eagerness to say it aloud. J. Crew was never as noisy, which was a matter of both aesthetics and brand positioning.

“The Kingdom of Prep” is, at heart, a business history, and it depicts J. Crew’s success, or, anyway, survival, as the result of individual genius. After the company cycled through a series of managers who lacked Cinader and Scott’s golden touch, it recovered some of its swagger in the two-thousands, under the leadership of Mickey Drexler. Famed for his tenure at the Gap, where he helped repopularize khakis, Drexler installed an intercom system so he could call in and address all his employees with his latest observations and riffs, even while out of town. In the late two-thousands, Jenna Lyons, a designer whose persona and eclectic personal style became synonymous with the brand, attracted a devoted following. Drexler and Lyons launched Madewell, a more trend-responsive line targeted at younger women, and, in 2008, introduced the Ludlow, a slim-fitting suit that remains one of J. Crew’s most popular products. Soon, a generation of thirtysomething men was overinvesting in gingham, chambray, and sports coats.

The brand’s public apex was the 2009 Inauguration of Barack Obama. His wife, Michelle, and their daughters, Sasha and Malia, all wore J. Crew pieces, making the brand seem like the affordable uniform for this hopeful, post-everything moment. The fact that J. Crew made clothes that you could wear from elementary school through adulthood contributed to the sense that this was a uniform for a new America. The next day, the company’s Web site crashed from a barrage of traffic. J. Crew was now firmly part of the establishment, and officially accessible to all. Lyons became the kind of celebrity influencer whose whereabouts were tracked on gossip sites. (In 2011, she came under fire by conservative media outlets, for a catalogue spread in which she painted her son’s toenails pink.) Almost single-handedly, she moved the brand from a fixation on Americana to a more eclectic, modern interpretation of prep, where khakis and cable-knit sweaters coexisted with sequins and oversized jewelry.

But already J. Crew was falling on hard times, as were many of its onetime competitors: Abercrombie, the Gap, even Brooks Brothers. Under Drexler, in 2011, the company took on immense amounts of debt after another leveraged buyout. And it struggled to respond to the rise of athleisure, casual workwear, and fast fashion, as brands like Zara and H&M—and, more recently, Shein—prospered by selling cheap, trendy clothes not meant to be worn more than a dozen times. A “retail apocalypse” hobbled brick-and-mortar stores; at the same time, J. Crew didn’t adjust quickly enough to the new expectations of online shopping.

In “The Kingdom of Prep,” Bullock laments the “never-ending fire sale” of the company’s recent years, when anything she wanted would be discounted within months, making the brand seem weak and directionless. In fashion, as with society at large, it seems as though the middle disappeared: consumers gravitated toward high-end luxury or fast fashion, not moderately priced uniforms for blending in with the establishment. Meanwhile, a considerable number of young shoppers have begun resisting the churn of new products altogether. A desire for ethical forms of consumption—bolstered by concern over one’s carbon footprint—has pushed many teens and twentysomethings toward secondhand clothing. (On the upscale side, venders include the RealReal and Rent the Runway.) It’s currently a thirty-billion-dollar market and growing fast.

Then, too, the nostalgic air of preppy style could acquire troubling resonances in an age of political fracture. When white supremacists descended on Charlottesville for the 2017 Unite the Right rally, for instance, many wore polo shirts and khakis as an expression of heritage. The effect, as the writer Amdé Mengistu described it, was “as if Quentin Tarantino had drunkenly shot a J. Crew catalogue.”

“The Kingdom of Prep” recounts an absorbing story from the viewpoint of the visionaries, and the “competitive, deeply bonded believers” who worked for them. Yet consumers are the ones who determine which ideas survive. In the 2022 podcast series “American Ivy,” the journalist Avery Trufelman argues that prep remains the foundation of American dress, which makes it an appealing template for everyone from Christian nationalists to the Lo Lifes, a group of Black and brown shoplifters from Brooklyn who became infamous in the eighties and nineties for their obsession with Ralph Lauren’s most exuberant designs. “The clothes were made for the upper-class preppy kids from Yale and Harvard,” Thirstin Howl III, a rapper and prominent group member, said. “And you know some kids from the ghetto just took it, remixed it, and we made it our own.”

I’m of a generation that believes Ralph Lauren peaked with his “Snow Beach” line, immortalized by Raekwon, of the Wu-Tang Clan, in the 1994 video for “Can It Be All So Simple.” Before rappers had the resources to build their own fashion empires, they often repurposed what was available to them, and in the nineteen-nineties the beneficiary of this was prep. The style’s route to fashion was through hip-hop, as rappers imagined new ways of wearing old clothes, giving brands like Polo, Tommy Hilfiger, and Nautica unexpected cachet that had nothing to do with dreams of emulating the Wasp life style. Because prep was always about resisting the winds of fashion, it was a turning point when designers like Hilfiger returned the love—Aaliyah famously starred in a 1996 Tommy Jeans ad campaign, and there were reports that a 1999 mixtape featuring underground rappers, all commissioned to rhapsodize about the brand, would feature a well-placed “Tommy!” to bleep out any offensive language. If clothes tell stories, the meaning of those stories is woven, sometimes unintentionally, by those who wear them as well as by those who make them. These days, I find myself trawling through Depop, a vintage resale site, hoping to rebuy some of my teen-age clothes, in the onset of a uniquely postmodern midlife crisis. The unlined plaid J. Crew jacket from the early nineties: maybe this prep relic can reconnect me to a kind of grungy, teen-age moxie.

Earlier this year, a fashion writer named Derek Guy experienced a curious uptick in his Twitter count. He’d built a robust following because of his expert opinions on subjects like cashmere sweaters and bespoke suiting, which he interspersed with jokey memes about Japanese workwear or hype culture. But now, owing to a change in Twitter’s algorithm, he began showing up in enough people’s feeds to warrant a series of articles about why “menswear guy” was suddenly everywhere.

Guy is opinionated about both classic, formal approaches to attire and contemporary streetwear. And he has long championed J. Crew as a low-risk entry point for men hoping to dress better; in one interview, he likened the brand to the best-selling radical historian Howard Zinn, describing it as a kind of gateway influence. A couple of years ago, J. Crew—having filed for bankruptcy early in the pandemic and undergone a period of restructuring—appointed Brendon Babenzien as its men’s creative director. He was formerly the design director of the streetwear brand Supreme and the co-founder and designer of Noah, and he opened a clubby concept store and coffee shop in downtown Manhattan. (It hosted a book party for me last fall.)

When Babenzien’s first J. Crew collection débuted to great acclaim, last July, Guy noted that the designs were virtually indistinguishable from more expensive, fetishized brands, such as Margaret Howell, Drake’s, Aimé Leon Dore, or Beams Plus. “If your purchases at ‘edgy’ brands like our legacy and visvim are limited to boxy tees and ever-so-slightly different jeans . . . you also look like you’re wearing j crew,” he wrote in a Twitter post. “Everyone is in jcrew. this is the reality.” Guy thought that J. Crew’s stigma as a “mid-tier” brand prevented people from appreciating this. J. Crew had become too accessible. Babenzien’s line—complete with a look book set at a lakefront boathouse, harking back to the brand’s roots—was a reminder of how interwoven the style had become with American dress, how ubiquitous its vibe was. As a business, J. Crew may continue to rise and fall, but as a sartorial sensibility its victory is secure. Whether as rebels or loyalists, we’re all fated to be subjects in the kingdom of prep. ♦