Not long ago, print subscribers to the New York Times received a special advertising insert with their newspaper: The first page featured a striking white background with a full-page photo of the ageless, gorgeous, uber-WASPY-looking model Carolyn Murphy in a white mini-skirt and polo shirt, clasping a gingham sun hat and insouciantly looking off into the middle distance as if searching for a tray of canapés. "J.CREWFORTY" was emblazoned at the top of the page, and the ensuing photos on the inside pages featured younger models in brighter colors wearing rugby shirts, trench coats, chinos, striped T-shirts, and other popular J.Crew styles.
The advertisement is part of a strategy to reintroduce J.Crew, which turns 40 this year and has only recently emerged from bankruptcy, to a new generation of consumers. A J.Crew executive told the fashion website Glossy that the company’s marketing theme this year is "timelessness." The ad copy in the anniversary insert plays up the theme: "Thank you for saving your old catalogues and Rollneck sweaters for generations to come. … Thank you for loving stripes and dogs as much as we do. Without you, there would be no J.Crew."
Without J.Crew, there would also never have been a mass-market for preppy fashion, or so argues Maggie Bullock in The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew. The fact that the "J.Crew style" is so easily identifiable even after 40 years is not an accident, and Bullock, a longtime contributor to Elle magazine, is a charming guide through what is fundamentally a business history. Luckily for the reader, Bullock enlivens the story by telling it through the lives of J.Crew’s founder, Arthur Cinader, his daughter, Emily, and the company’s two later leaders, or "cults of personality" as she describes them: former Gap CEO Mickey Drexler and Jenna Lyons, who rose through the ranks of J.Crew to become its undisputed creative force in the 2000s and 2010s. Bullock’s tale "connects the dots from the catalogue boom of the ’80s to the specialty retail bonanza of the ’90s, through the birth of online shopping, and into an era in which we shop from phones that never leave our hands."
According to Bullock, J.Crew managed for a time to dominate the mass market for aspirational dressing, which she describes as invoking "the delicate brine of a clambake wafting in the air; the particular romance of a misty morning at a rustic lakehouse." She captures well a particular moment in fashion in the 1980s, when Lisa Birnbach’s satire, The Official Preppy Handbook, became a bestseller and inexplicably morphed into a kind of lifestyle Bible for the masses, with its descriptions of the "Tretorn sneakers, signet rings, ribbon belts. Shocking-pink Lilly Pulitzer bikinis. Popped-collar Lacoste shirts" that defined preppy style. "Preppy" was a kind of unofficial uniform that signaled its wearer’s status as having made it, "all part of a nonchalance about wealth," Bullock notes.
But nonchalance appeals even to those who don’t have the inherited wealth to justify it. Egalitarian societies still enforce class boundaries; they just do so through social signals that can be bought, not only inherited (hence the 19th-century anxiety about being hoodwinked by "confidence men" who dressed like gentlemen but were anything but). As Bullock argues, "strivers had long masked the anxiety of improving one’s station in life by adopting the look of belonging, the look that made them fit in at the country club, the sorority house."
Such aspirational dressing was not merely about being able to purchase a particular item, but rather it was the promise (or, more aptly, the mirage) that one might be able to enjoy the lifestyle of those who wore it. I recall, as a born-and-raised Floridian utterly ignorant of fashion, my first encounter with this old money style, at summer camp in Vermont in the 1980s. My denim shorts and neon-colored T-shirts baffled my fellow campers, as their old sweatshirts with foreign words such as Groton and Choate on them perplexed me. Everything they wore was faded or comfortably worn-in, yet somehow never disintegrated in the laundry like my Busch Gardens T-shirt did after only three washings. Their clothes suggested ease and quality and, yes, money—but with a whisper, not a shout; soft chambray, not garish logos. These were people who instinctively knew how to pronounce "gunwale" as "gunnel." J.Crew successfully bottled and sold this formula to consumers for decades, a "lifestyle that was enviable, but also relatable."
It was not always smooth sailing for the company. Bullock dives into the prickly personalities of Cinader and the cool aloofness of his daughter, Emily. Without their distinctive vision, J.Crew would have languished as a catalogue company (like L.L. Bean or Land’s End) rather than becoming a uniquely stylish mass market brand with stores nationwide. But their "unyielding perfectionism" could generate tension among employees. "At J.Crew, it was her way or the highway," Bullock says of Emily’s reign.
It was Emily who insisted the company "make a catalogue that didn’t feel like a catalogue, with images as good as the ones in fashion magazines." She succeeded. For at least a decade, J.Crew’s catalogues featured the kind of images that made consumers want to become the people in distressed chinos and madras shorts who walked their perfect Golden Retriever along the beach or laughed while trimming the jib on their sailboat. In the age of Instagram, it’s easy to forget how radical it was for the creators of a clothing catalogue to ask of their images, "Does it feel real? Could it pass for snapshot?" Similarly, J.Crew can be credited (or blamed, depending on your opinion) with launching the trend for pretentious color names for its clothing: ochre, palamino, cedar, nutmeg. In a J.Crew catalogue, nothing was ever simply brown.
By the 1990s, J.Crew had shifted to offering high-quality yet affordable basics (better than the Gap but less expensive than Ralph Lauren) and began embracing the minimalist dressing of the era; it had also become distinctive enough as a brand that it was parodied by Spy magazine and featured in cartoons in the New Yorker. It was shipping 17 catalogues every year to more than four million households. But it was not making much money. Bullock dutifully chronicles the many business missteps and revolving door of management figures who tried to right the ship. Eventually, former Gap wunderkind Mickey Drexler was brought in to lead the company.
Bullock tries the patience of the reader with a deep dive into all things Drexler: his background, his previous work history, his motivations, his grudges. Her enthusiasm sometimes lapses into cliché ("Mickey moved like a freight train," "All eyes were on Mickey"). She clearly admires Drexler’s verve and business instincts and credits him with pushing J.Crew into an era where its brand became a fusion of both "true, unadulterated prep" and "affordable luxury."
Likewise, Bullock gushes a bit too much over J.Crew design guru Jenna Lyons, whom Drexler elevated to the role of president. "No one had found a way to market ‘personal style’ to the masses," Bullock notes, until Lyons. Lyons was in charge of rebranding J.Crew yet again, which she did to great effect, using her own quirky style as the lens through which this latest iteration of preppy would flow.
A fortuitously timed appearance by Michelle Obama wearing head-to-toe J.Crew on The Tonight Show, followed by Obama’s children sporting colorful J.Crew coats for their father’s first inauguration, was an unexpected marketing coup for the company. The first lady would frequently don J.Crew during her husband’s time in office, and for a time, the company’s stock rose both literally in financial circles, as well as in style circles.
Lyons’s star rose as well, creating new tensions: "J.Crew had wanted a celebrity designer. What they got was a full-blown celebrity," Bullock notes. Soon the catalogues featured "Jenna’s picks" and models that looked eerily like Lyons herself. Lyons launched a high-end J.Crew "Collection," and for the first time, J.Crew presented its clothes during New York Fashion Week. Lyons’s legions of fans blogged about her style but sometimes questioned the wisdom of some of J.Crew’s products. "Was anybody out there actually buying $358 snakeskin heels from J.Crew?" one blogger asked.
It was a question that leaders at the company began to ask as well, especially after Lyons’s personal life became tabloid fodder and sales began to slump. Lyons leaned into her newfound celebrity. "Old Jenna had been stylish, but sweet," Bullock writes. "New Jenna was chic" but also increasingly out of touch with J.Crew’s DNA and its employees. "She turned into, like Jenna," one former employee told Bullock, "this fashion lesbian icon" who attended the Met Ball and the nuptials of Solange Knowles. As fashion website Racked asked, "Is the cult of Jenna Lyons eclipsing J.Crew?"
As with all things fashionable, trends change. Jenna’s much-copied style grew stale, and customer interest shifted. Bullock quotes a copywriter who dispensed harsh wisdom about the new, younger consumer, who increasingly bought clothes online: She "doesn’t want to read an entire fucking essay about how their sweater got its name. … She doesn’t have the attention span for that."
Bullock gamely covers J.Crew’s foundering in the 2010s and its many causes: "Sale-addicted shoppers. The slow death of the mall. The tractor-beam pull of Amazon." She astutely notes that the "fancy stuff" promoted during the Lyons era overshadowed the basic clothing that guaranteed the company’s bottom line. "It made people think J.Crew was more expensive than it really was." Consumers also complained that the quality of the clothing had declined, something J.Crew’s leaders vehemently denied, further alienating its customer base. That customer base was also getting larger in size, if not in number, a fact J.Crew also didn’t accommodate. As Bullock notes, "67 percent of American women could not shop J.Crew clothing at all because they were a size 14 or larger."
Eventually, the slow-rolling retail apocalypse claimed another victim. Amid waves of downsizing, layoffs, and rebranding attempts, both Drexler and Lyons left the company. In 2020, J.Crew declared bankruptcy. By 2021, Bullock writes, "J.Crew mall stores were being repurposed as COVID vaccine clinics."
Bullock’s last chapter is an unfortunate and overwrought exercise in virtue-signaling that reads as if it was tacked-on to assuage the demands of liberal readers. To cite one example: Bullock describes a widely circulated news photo taken of St. Louis residents Mark and Patricia McCloskey in the summer of 2020. The couple were brandishing guns and standing in front of their house while Black Lives Matter protesters marched by. He was wearing chinos and a polo; she was wearing a nautical-striped T-shirt; in other words, preppy personified. Bullock’s conclusion? "To anyone who cared about being on the right side of history, the uniform of the establishment had a newly toxic undertone."
Readers would have benefited far more from a conclusion that returned to the larger question of how clothing serves as a form of status-signaling in a democracy and what place mass-retail has in that process. Is there a future for mass market aspirational fashion, or has athleisure conquered the world? Is preppy dead or merely dormant (or, in its current incarnation on TikTok, gone completely nuts)? Or, as a long-ago J.Crew customer might have asked while gazing at the beautiful people romping around the pages of a catalogue: Will a rollneck sweater and "pre-distressed" chinos change my life?
The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew
by Maggie Bullock
Dey Street Books, 368 pp., $29.99
Christine Rosen is a senior fellow at the American Enterprise Institute