On a sun-dappled summer day 10 years ago, a balding, slightly manic man threw open the door of the J. Crew Collection boutique on the corner of Madison Avenue at 79th Street and made a beeline for the first employee he spotted. “Hey, who are you?” he demanded of a college student—let’s call her Emma—re-folding the stack of cashmere sweaters she’d folded a hundred times that summer. “Um, Emma?” she replied. “Emma! We have Emma!” the man exclaimed, his Bronx accent reverberating through the almost empty store. She looked around. Who was “we”? “O.K., Emma, whaddya think—how are we doing with these sweaters?” It took a second to spot his cell-phone headset, and another to realize that Millard “Mickey” Drexler, her boss’s boss’s (boss’s boss’s) boss, was conferencing this impromptu recon session back to corporate. Only later would she learn that such calls were piped through the entire company HQ, via Drexler’s infamous intercom system. Emma wasn’t just talking to the C.E.O. of J. Crew. She was talking to all of J. Crew.
In corporate fashion, where decisions tend to be handed down like decrees, Mickey Drexler reveled in the scrum. For 14 years, he paced—and sometimes biked—the halls of J. Crew’s multi-story headquarters near Manhattan’s St. Mark’s Place, interrogating everybody he came across: salespeople, designers, the mail guy. Over fried artichokes at Morandi, or in the office, over sliced peaches he had flown in from California, he peppered business talk with colorful tales about, say, the submarine he once toured with the founder of Under Armour. When it was time to choose the cover of the next catalogue, he convened a room of employees and put it to a vote. Sure, everyone knew this was mostly an exercise—chances are, the creative whizzes would talk Mickey into the cover they’d picked from the get-go—but so what? Everyone was game. If you worked for Drexler, you did not merely pocket a paycheck. You wore, lived, breathed J. Crew. Quips a former employee, “We were a bunch of not-as-cute catalogue models.”
Here’s the thing about Kool-Aid drinkers: they work hard. Together with designer Jenna Lyons—his right hand and the brand’s creative engine throughout most of his tenure—Drexler built a team that breathed an unlikely second life into a mid-tier catalogue label, erecting a powerhouse that enjoyed an extended stretch near the top of fashion’s roller coaster. That stretch made Drexler rich—or richer, anyway. It made Lyons famous: she is as recognizable as Donna Karan, Vera Wang, or Tory Burch, women with their own names on their doors. And in what had been a dead zone between designer and mass fashion, it gave American shoppers a conveniently located, approachably priced land of not-so-basics (peppy, preppy cropped Minnie trousers; slim Tippi sweaters) with real mojo (sequin-dappled tanks, cropped jacquard party pants)—so much so that buying them could feel a little like buying, and buying into, Fashion, or something convincingly close to it. For a time, J. Crew conjured a blend of relevance and emotional resonance that any brand, at any price, would kill to achieve.
But as anyone who has entered a J. Crew store recently can tell you—and as many insiders asserted in interviews— the only discernible feeling the company has evoked in recent months is ennui. The clothes and the imagery that once made them covetable have become ho-hum, somehow drained of spirit. And the headlines surrounding the company have been even worse. Since 2014, J. Crew has been steadily clacking back down the tracks it once ascended, shedding money and influence, not to mention executives—most notably in 2017, with the exit of Lyons, Drexler, and longtime men’s-wear designer Frank Muytjens. When that losing streak continued this past November, with the departure of the guy who’d been brought in to fix it, C.E.O. Jim Brett—who lasted a mere 16 months—the forecast appeared ominous. Brett’s tenure had been tumultuous and, to a team still loyal to Drexler and Lyons, bruising; senior employees report feeling as if they had a new boss every week. After Brett left, the company spent months in a no-man’s land, run by a committee of executives described rather uninspiringly as the “office of the C.E.O.,” its fashions designed until this past winter by Johanna Uurasjarvi, whose imprimatur, even to many inside the company, was hardly felt. All of which seemed possibly irrelevant anyway, given rumblings in the business press about an insurmountable debt that, according to a source in a Washington Post article, makes any turnaround plans the equivalent of “rearranging deck chairs on the Titanic.” In addition to that nearly $2 billion debt load, the company reported a net income loss of $120 million for the last fiscal year.
Starting in February, J. Crew began implementing its latest attempt at self-preservation. The company named 36-year-old designer Chris Benz S.V.P. of women’s design. For Benz, who is coming off a four-year stint running the relatively small label of American sportswear legend Bill Blass, the gig is a homecoming of sorts. When he was fresh out of Parsons School of Design, Benz spent more than a year working under Lyons and Drexler at J. Crew, before departing in 2006 to launch his own now-defunct collection. Appointing a fashion-world darling known for his courtly charm and his penchant for undiluted color has the potential to both reinvigorate the aesthetic and stanch the bleeding. Even in his first few months on the job, Benz’s presence has inspired some optimism within J. Crew’s dispirited ranks. But Benz is somewhat untested, and the company’s empty throne—vacated by the enormous presence of Drexler—remains only partially filled. In April, after talks to woo former Ralph Lauren C.E.O. Stefan Larsson fell apart—due, it is said, to Larsson’s belief that the company coffers are too depleted to execute the necessary turnaround—J. Crew announced the appointment of an interim C.E.O., former president and C.O.O. Michael J. Nicholson, who had been one of the foursome running the “office of the C.E.O.” The highs and lows of J. Crew tell not just a tale of a retail giant now desperately in need of re-invention—though they do that, too—but one of power, personality, and the evolution of American style.
J. Crew was born in 1983, three years after Lisa Birnbach crystallized the world of boarding school, Top-Siders, and pearl-wearing Muffys in her seminal Official Preppy Handbook. Founder Arthur Cinader conceived J. Crew as a chicer women’s alternative to newly successful cataloguers Lands’ End and L. L. Bean—that would sell the Ralph Lauren look at half the price. Ralph had already laid claim to the landed-gentry sport of polo, so Cinader settled for crew, added a J for flourish, and shot the first catalogue at Harvard’s Weld Boathouse, home of the women’s crew team. J. Crew has always been about context, and viewed in the bosom of casual privilege, simple roll-neck sweaters, weathered chinos, and rough-hewn barn jackets spoke to Ivy Leaguers and aspirants alike. The brand became, as The New York Observer once noted, a “proselytizer for the sun-splashed, ruddy-cheeked American Dream”—in an America that extended precisely, according to a 1989 catalogue, from “Kennebunk to Nantucket, Narragansett Bay to Amagansett, and points South and West.” (South and West being, presumably, Connecticut.)
Over the years, countless style tribes have adopted, deconstructed, and reconstituted whatever “preppy” means, but at its core, J. Crew has always implied collegiate, polished, privileged. The narrowness of the world the company first opened a window to is now, thankfully, a thing of the past. There is no one way to look or dress “American.” So how do you resuscitate a brand built on this definition? And is there still room for it?
The son of a Garment District fabric-and-button buyer, Mickey Drexler grew up sleeping in the foyer of his family’s Bronx apartment and dreaming of finer things. He started out at Bloomingdale’s earning $11,500 a year, made his name at Ann Taylor, and beginning in 1983, engineered a turnaround that made retail history. At Gap, Drexler overhauled Banana Republic; launched bread-and-butter offshoot Old Navy; and, at the mother ship, even made the humble khaki seem kinda sexy. A $480 million jeans-and-tees business morphed into a $14 billion behemoth, earning Drexler a sobriquet that has stuck: the Merchant Prince. But in 2000, sales plummeted; stocks sank more than 75 percent. In 2002, Drexler was out.
Drexler took his $100-million-plus in Gap stock and bought, among other things, his own Gulfstream. But he passed over a multi-million-dollar severance package that would have entailed a non-compete clause. The Merchant Prince wasn’t going out like that. Within months, he’d taken over as chairman and C.E.O. of J. Crew. It was less than one-twentieth the size of Gap, and had just cycled through four C.E.O.’s in five years. But.
The day Drexler walked in the door, every employee knew they were auditioning for their jobs. Drexler had been tipped off by a colleague to look out for Jenna Lyons, then V.P. of women’s design. On day two, he had her go through a lineup of new looks, selecting only the items she believed in. As rejects piled up, “I was so confused, and I was scared, but I was also a little bit excited,” Lyons later said. “All the things that I liked and that I thought were brand-right he was leaving up on the wall. And I was like, Is that good, is that bad? I don’t know.”
The brand’s beleaguered design team, accustomed to a spreadsheet mentality—churn out X chinos in Y colors, repeat—were suddenly given what felt like creative carte blanche. Drexler “put the product and the design before the business, in a way,” recalls a former employee. “He made the creative drive the business.”
Drexler once told a roomful of employees that he’d passed on a hire because the candidate didn’t know the meaning or origin of her high school’s name. How could you go someplace every day and not be curious enough to figure out where the name came from? Drexler stayed five steps ahead, and for those who could keep up, the sky was the limit: invent a new product, a new category, a new business within the business. And if you can’t keep up, get the hell out of the way.
Early on, Drexler brokered a deal to sell cashmere by the luxury Italian firm Loro Piana at a friendlier price. To the wealthy, used to dropping $800-plus for real-deal Loro Piana at Bergdorf’s, $220 cashmere was adorable. To the many who were not, it was doable. Now that J. Crew could brag about selling real Italian cashmere (stitched in China, but whatever), a Venn diagram could be traced between what had been two disparate camps: luxury consumers stocking up on staples, and mass consumers buying something special. Suddenly, shoppers on both sides of the spectrum badly wanted the same thing. Here, you could see the power of the catalogue—still shot mostly on location, in spreads as lavish as those of a fashion magazine—in which Drexler’s Kool-Aid-drunk copywriters waxed poetic about provenance and ply, defining and redefining that Waspy consumerist dog whistle, “investment pieces.”
At times, 770 Broadway felt like Sunset Tower, as the boss paraded around whatever famous person—A-Rod, Ina Garten, Bette Midler, Jimmy Fallon, Bono, Kate Hudson—had come to seek his business advice, or just to check out the scene inside of J. Crew. Once, Drexler called in and, over the intercom, told the whole office he was hanging out with “Feral.” (This turned out to be Pharrell.) That intercom, as omnipresent and disruptive as the squawking principal’s office P.A. system of yore, was his unsubtle way of keeping an entire company both slightly on edge and immersed at all times in his own rapid-fire mental stream. Day in, day out, he flicked it on, whether to play the Springsteen song that had just popped up on his iPhone, or to share a meditation on something he’d spotted “in the atmosphere,” as he put it—the violinist character in the movie he just saw; the service at the restaurant where he’d just eaten—that might, in some obscure way, inform their work at J. Crew.
Early on, he identified a core group of people steeped in J. Crew’s DNA. Anytime he wanted to get rid of something that he felt was wrong for the brand, he’d page the “heritage team” over the loudspeaker. “That group would go posthaste wherever he happened to be, no matter the location in the building. He wanted their opinions,” Lyons recalls. “The collective feedback provided a real-time ‘temperature check.’ ”
Lyons proved singularly useful as a filter for Drexler’s rat-a-tat ideas—and eventually, as the only person who could reliably talk the C.E.O. off a ledge. She also possessed an unswerving sense of what was and was not J. Crew. Chinos and T-shirts took on a new exuberance: the pants were frayed, the top splattered with paint. Add a fuchsia blazer on top, collar popped, because why not? To this day, competitors use “J. Crew” as an adjective to describe stripes paired with florals, or sneakers with trousers. When deconstructed, the look consisted of straightforward clothes that everybody knows how to wear. But as assembled by Lyons and longtime head stylist Gayle Spannaus, who departed this spring, the mashup had an irreverent, often tomboy cool that up-ended the neutered boys’-school look of Alex P. Keaton-era prep. As time went on, the amalgam became increasingly adventurous, experimenting with color—shimmering, saturated, mood-lifting—and proportion, pushing a mishmash of prints, sprinkling nighttime sparkle over daytime separates, matching wedding dresses with Wellies. Lyons gradually established a creative monarchy in which she O.K.’d everything from the crimson-lipped models in the catalogue to the light fixtures in the boutiques, to those peppy promo e-mails that kept popping into your inbox, day after day.
By 2008, Drexler had made Lyons J. Crew’s creative head. Two years later, he gave her the additional title of president—a joining of church and state that is generally avoided in fashion, especially for an employee who is neither founder nor namesake.
By the late aughts, fashion people—editors, stylists, hangers-on who until then had been famous mostly within their own self-referential bubble—had become a more general source of fascination, rabidly documented by photographers like Scott Schuman (@thesartorialist) and Tommy Ton (@tommyton). The era of the street-style star fed into the era of the Influencer, and here was J. Crew, sitting on a gold mine: its own bona-fide Fashion Person. Lyons had both glamour—trotting down red carpets in feathered maxi skirts—and a disarming relatability. She was neither the hot new thing plucked from the ranks of a European fashion house, nor the indie darling creating buzz at the helm of her own label. She was a smart, talented woman from a working-class background who spent her whole career working her way up at a mall brand, and then she got famous for it.
To people who had worked with Lyons for years, her transition to famous person was organic, and yet no accident. She adopted a signature look: thick fashion-nerd glasses; sharply parted, slicked-back hair; slim tailored jackets; and plunging necklines, sans bra (in and out of the office). Lyons—who is, by all accounts, both a brilliant designer and no slouch in the business department—told colleagues she was determined to read more, to improve her vocabulary. None of this made her any less likable. “She had always been really funny and self-deprecating,” says a former colleague, “but she was in pursuit of something. She wanted to better herself. It was all media-trained.” When Lyons’s Brooklyn brownstone landed on a 2008 cover of Domino, igniting a Pinterest craze for yellow velvet couches, it was apparent inside the company that their aw-shucks leader had become something new: Jenna, “this, like, fashion lesbian icon.” In 2014, Lyons played Hannah Horvath’s boss in a cameo on Girls. Two years later, Jenna fever hit its apotheosis when Hannah Horvath turned around and played Jenna. Well, sort of. That May, Lena Dunham and producing partner Jenni Konner were Lyons’s guests at the annual Metropolitan Museum of Art Costume Institute Gala. All three showed up dressed as Lyons herself: matching razor-sharp J. Crew suits, thick glasses, slick hair, swooping décolletage. The gag was Dunham’s idea. It was a very meta Met Gala moment.
That year, Lyons scored the cover of Fast Company under the headline HOW JENNA LYONS TRANSFORMED J.CREW INTO A CULT BRAND. It’s hard to imagine better press. “Not since Steve Jobs and Jonathan Ive at Apple,” raved the magazine, “has a creative pairing been as intriguing and fruitful as that of Drexler and Lyons.”
Many J. Crew insiders saw zero evidence that Drexler resented Lyons’s rising star. After all, he had her creative vision to thank for the company’s ascendance. A source close to Drexler says the Fast Company cover was his idea, part of a quiet but concerted campaign to make it evident to all that Lyons was his business partner, not just the designer—and, with Drexler’s own retirement on a not-too-distant horizon, that she was even C.E.O. material. As Team Mickey saw it, if the boss had any reservations about Operation Jenna, it was because, with her private life becoming increasingly public—stories floated around about her floating around on blow-up swans at high-profile Manhattan pool parties—he felt a sense of paternal protectiveness. Others say, Yeah, right. For the man at the top, watching Jenna get all the credit for J. Crew’s success was too much. “I remember, he was like, Enough with the Jenna press: You need to cool it. You need to lay low,” says a former employee. “He got very territorial and jealous.”
Legend has it, Drexler unleashed his ire about Fast Company on a J. Crew executive, who—in a maneuver straight out of The Devil Wears Prada—dispatched a team of employees to scoop up every copy of the magazine off New York City newsstands.
This mission was covert, desperate. Irrational even: the magazine was on newsstands across the country; what was taking it off a few Hudson News racks going to do? Team Mickey maintains that the C.E.O. himself never knew it happened. But even those who chuckle at the drama of it all concede that Drexler was never short of yes-men happy to do his bidding—no matter how absurd. Says a former J. Crew employee, “No one believes in their own abilities more than Mickey Drexler, except probably the man in the White House.”
When Drexler took over J. Crew in 2003, you didn’t need the term “brick-and-mortar” to indicate that a store physically exists. Amazon was still a newfangled online bookstore. Cell phones barely took photos. When you needed jeans, it’s possible you ordered them online—J. Crew launched e-commerce in the dark ages of 1996, well before Drexler even arrived—but chances are you still went to the mall. Nostradamus himself could not have predicted the massive cultural forces that would rock mid-tier American retailers like Gap, Banana Republic, Ann Taylor, and J. Crew. But if a single development knocked them all off their game, it was the invasion of European fast-fashion mega-brands. By the late aughts, H&M and Zara were flashing supermodel-stocked ad campaigns and, thanks to a global reach and lightning-fast factories, cranking out runway trends virtually overnight, for cheap. This was a threat that J. Crew’s promise of craftsmanship, detail, and lasting quality was not built to withstand.
Online, shopping decisions are based on one factor: price. If you can buy cashmere for $39.90 at Uniqlo, you don’t need a lyrical essay about a Himalayan goat to sweet-talk you into it. Will that sweater last? Probably not. But by 2013 or so, shoppers had gotten hungry for a new look for every Insta post—not a sweater for the ages.
Those who care about the durability and provenance of their basics had new “digital natives” to buy them from. At Everlane, a desirably bland sweatshirt comes with the halo of millennial authenticity and next-level convenience. It’s not like Drexler and Co. didn’t know how to play this game: Drexler still sits on the board of two of this genre’s biggest success stories, Warby Parker and Outdoor Voices. And J. Crew’s little-sister brand, Madewell, the one very bright spot on J. Crew’s balance sheet—so bright, in fact, that the company is now investigating the possibility of its IPO—was launched in 2006 as a digital-era enterprise with a much more targeted customer base (essentially, millennial denim). Madewell has also built a consistent relationship with a few signature causes: recycling denim and Habitat for Humanity. Check, check, check. But no one at J. Crew HQ—nor anyone at its competitors, for that matter—could crack the code on how a comparatively sluggish, decades-old mega-brand stays true to its DNA while also “pivoting,” as the kids say, like an invented-yesterday start-up.
There were plenty of reasons why one might have predicted that at some point Drexler and Lyons’s formula would stop working. But when it did, the change seemed sudden, and irrevocable. To Drexler, it must have felt like déjà vu. In 2014, after 11 years of mostly incline, J. Crew plummeted, reporting losses of $607.8 million.
Overnight, it seemed, the knives were out: J. Crew was out of touch, critics ranted. Over-styled, overpriced, elitist. Too geared toward the moneyed cool of coastal creatives. A red vs. blue theory emerged in which flyover-staters, finding themselves priced out, were not just mystified by the suggestion of a spangled blazer for work, but deeply pissed off by it. Who did the people making these clothes think they were?
“You are pretty dope in your tireless collections of one-season-wear floral patterns,” wrote Oregon-based writer and illustrator Tricia Louvar in an “open letter to Jenna Lyons” that went viral in 2015. Louvar, “an ordinary mother on a modest income,” tallied the price of an “everyday” J. Crew outfit: $596, the equivalent of 298 school lunches.
The company found there were downsides to a mass brand tethering its identity to a creative, freethinking New Yorker who had penetrated fashion’s inner circle. Lyons’s personal life had been “Page Six” fodder since 2011, when she and her husband divorced, and she started dating jewelry designer Courtney Crangi. There was also the time she painted her young son’s toes pink in a picture that ran in the catalogue. Jon Stewart dubbed the controversy “Toemageddon.” It sounds benign, but “people freaked the fuck out,” says one of Lyons’s former colleagues. “You’re not immune to conservatism—that’s most of the country.”
With her TV cameos and $2,500 sequin skirts, Lyons made an easy scapegoat for the brand’s sudden woes. But insiders say that what really incensed the customer was not tone-deaf pricing, but something a little harder to spot (and own up to): prices had crept up, while quality, many say, was declining. “There was a real drive to increase margins every season,” says one former employee. In meetings, Drexler—following his gut, as ever—would ask the same question over and over: What are you selling this for? If it was $49, his response was, Can you do $59? How about $69? And so on. Of course, you don’t get to be the Merchant Prince without always asking: how can we make more money? But Drexler’s relentless up-pricing had consequences. Says this insider, “A men’s shirt that cost $49 in 2012 had by 2014 edged up to $75 or $80.”
“Here we were screaming from the rooftops about how well-made this stuff is,” says a former employee. “Then you start to get tons of feedback: ‘I just washed this sweater once and now there’s holes in it.’ ”
If J. Crew’s selling point was fashion-forward novelty, that was a game Zara was destined to win. And if it was quality? Well, if your $12.99 H&M sweater has a hole, you got what you paid for. But $220 at J. Crew? That better fucking last.
To the end, both Drexler and Lyons believed these were great clothes that people would be excited about and willing to pay for. When that stopped being the case, a staffer says Drexler seemed angry, but also genuinely baffled: “Mickey was like, These are novel! They’re colorful! They’re well-made. What is wrong with people that they don’t want them?”
J. Crew was not playing Chopin while the Titanic went down. New business models were launched (New York City’s much-lauded men’s-wear boutique the Liquor Store—R.I.P., as of March) and low performers were shuttered (the widely lamented death of bridal). McKinsey consultants were enlisted. The frequency of the catalogue was dialed back. But employees say that Drexler, for all his curiosity, was not always adept at listening to the answers to his own questions. Some saw him dismiss ideas that were later revealed to be prescient. “The reality was that the only opinion that counted was Mickey’s, and even when he was asking for your opinion, you’d usually get about two and half words out of your mouth before he was onto a different question or a different person, or he just told you outright: That’s a stupid idea.” In meetings, some say Drexler was unapologetic about his own unfamiliarity with the J. Crew Web site, and with online shopping in general. The company was late to jump on the Instagram train and failed to invest in new platforms that would have kept its site cutting edge. Says one longtime employee, with affection, “Mickey is an older man. If he didn’t understand it, he might have dismissed it, you know?”
J. Crew had weathered downturns before. But in the past, as soon as economic winds shifted, things had tacked back on course. So maybe Drexler and Lyons had reason to believe they could lash themselves to the mast, keep doing what they were doing, and wait for calmer seas. Whether it was due to Drexler, Lyons, or both, J. Crew stuck to a notion of glamour that was quickly becoming bygone. A holdover from the yacht-club aesthetic of the catalogue days, this carefully curated, cultivated image was embodied by a very specific kind of fashion-world model. To the company’s credit, the J. Crew “girl” was no longer necessarily white, but she still had a kind of girl-next-door-but-better (read: skinny) uniformity. One employee recalls a time the team strayed from this formula, casting non-models with diverse body types. Drexler hated it. “He was like, I don’t wanna be that person,” recalls an employee. The images were re-shot. A change was afoot that Drexler’s legendary gut did not check: Customers no longer wanted to look like one type of woman. And they no longer wanted to look like a brand—any brand. They wanted to find the style they liked at the lowest price they could find online. In failing to spot that shift, says one employee,“that’s when we showed our age.”
Viewed from a purely financial point of view, it’s remarkable how long Drexler’s decline was allowed to drag on. On paper, the company certainly could not afford a wait-and-see approach: an enormous pile of debt makes “almost everything the company does at the front end—stores to products—a little bit immaterial,” argues retail analyst Neil Saunders, a managing director at GlobalData.
In 2011, five years after he took the company public, Drexler took it private again, in a deal that barely passed regulators’ sniff test. Drexler spent seven weeks engineering the $3 billion leveraged buyout with two private-equity firms, TPG—which had a long history with the brand—and Leonard Green & Partners, before he bothered to inform the board, a strategy that is, at best, highly questionable. Just as the deal was about to close, the investors lowered their offer. The board was left with two choices: take it or leave it. When the shareholders sued, the Delaware judge who presided over the case described the conduct of Drexler and Co. as “icky.” The company agreed to a $16 million settlement and reopened bidding. But with Drexler really only interested in the players he’d singled out from the get-go, it was no surprise when no other bidders emerged. The $16 million penalty the company paid amounted to a wrist slap—one partly covered by insurance. When the deal closed, Drexler got off relatively scot-free, and reportedly more than $200 million richer.
But when sales began to plummet, the consequences for J. Crew were dire. The company found itself $1.7 billion in debt. It bought a little time in 2017, pushing back the maturity of some of its debt from 2019 to 2021, but every quarter it pays the piper some $35 million in interest. “Which means that even if they improve sales a bit, even if they get margins up a bit, they’re still making quite big losses every quarter,” says Saunders.
In 2017, after 10 quarters of declining sales, with debt hanging over everything like a low, impenetrable cloud, something had to give. Both Lyons and Drexler knew it. Insiders say that by this time it had become apparent Lyons would not be the right executive to turn the ship around, and that Drexler wanted to engineer a soft landing for her before another C.E.O. entered the picture. Which is what happened, with a minor hiccup: Lyons was tripped up by her own fame. When a tabloid caught wind that she’d been gabbing about her plans for life after J. Crew, her exit strategy fast-forwarded. Lyons was out that April, after 26 years with the brand. “How Jenna Lyons got too big for J.Crew’s britches,” cackled the New York Post, echoing a widely held assumption that the designer was taking the hit for the downturn and had been pushed out. Soon after, Drexler stepped down as C.E.O. But the Merchant Prince was hardly done with J. Crew: He stayed on until this January as chair of the board. Even now, he retains 10 percent ownership. (Drexler declined to be interviewed for this story.)
Today, Lyons—who is preparing to launch her own lifestyle brand with WarnerMedia—remembers the scrutiny as “humbling.” “It made me deeply aware of my impact, both positive and negative. I did my best. I am human—I made mistakes along the way.” In a way, she says, knowing that the world was watching “sharpened us all even further—we became obsessed with trying new things and bringing the best products to our customers.”
Within J. Crew headquarters, the most shocking part of the two years since Lyons’s exit has been how quickly the specificity of the brand they believe in has been decimated. Under Drexler-successor Jim Brett, many long-serving members of the team abandoned ship. And while J. Crew made some social progress (for starters, it began shooting clothes on a wider range of body types), it also spent millions launching smaller “sub-brands” with the idea of having something for everyone. Brett also purposely swerved away from J. Crew’s prescriptive how-to style. Circa 2018, dictating how customers “should” wear their clothes felt undemocratic. Preaching about provenance felt self-aggrandizing at best. In branding, as in life, telling everyone how great you are can feel … smug. So J. Crew swung the mirror around to the customer—instead of being self-referential, the tone became deferential: You, amazing individual, show us how you do it. But with the styling dialed down, and the marketing tactics curbed, the magic evaporated. J. Crew was selling what anybody could see were just crewnecks and anoraks. “There was room to improve. Our image was a little elitist, a little posh, very homogenous,” says a J. Crew staffer. But the tabula rasa approach proved to be an overcorrection, a classic baby-with-bath-water scenario that drained the brand of all point of view.
Does Chris Benz have both the vision and the force of personality to fill the void? Maybe. Benz, who for years was known for his signature highlighter-pink hair, is one of fashion’s beloved sons. Today he looks a little like a J. Crew 2.0 model himself, with his mussed hair, now dark, and camera-ready smile. Both his professional and personal aesthetic suit J. Crew—though they’ve never before been aimed at the mall-going segment of the population. Chris Benz, the label, which he ran from 2007 to 2013 with some fanfare and a lot of love from a certain stripe of famous woman—Eva Amurri Martino, Mickey Sumner, Elettra Wiedemann—specialized in bright, optimistic, often playfully patterned pieces, positioning Benz as a color evangelist, a cool kid who talked LBD-loving ladies into canary yellow. And Benz comes with his own Domino moment: his Brooklyn town house is already Instagram-famous.
So yes, Benz brings goodwill to a brand that needs exactly that. He might not need all the rest. Out of the gate, his purview is far narrower than Lyons’s was, and much is presumably resting on the incoming executive ranks. (A J. Crew spokesperson declined to make Benz or any executive available for interviews.)
Along with Benz came creative director Mark DeMott, an employee favorite who worked under Lyons for more than a decade and whose quiet return is seen internally as an effort to recapture some of the lost Lyons magic. At a company the size of J. Crew, it can take up to a year for the work of a new designer to be reflected in the store windows we see; customers might not get their hands on looks designed under Benz and DeMott until early next year. Still, at least one high-level employee asserts that the brand is, bit by bit, getting its groove back. You can see it already, in the models on the site who are once again actually smiling.
J. Crew is a big company that feels, on the inside, like a small one. “Everyone says there’s more than a glimmer of light,” says this employee, with unmistakable relief. “It’s like, we’re doing it. We feel like we’re doing it.”
Many of the employees who spoke for this story noted that they often heard from customers that J. Crew marked a first in people’s lives—the anorak they packed for college; the suit they bought for their first job interview. That’s not because the suit—or the barn jacket, or the roll-neck sweater, or that inescapable men’s checked button-down—was so groundbreaking. It’s because J. Crew, at various times in its 36 years, has struck an emotional chord. Maybe you aspired to master Lyons’s empowered mixing and matching. Or Michelle Obama’s perfectly nipped and belted sweaters. Or you’re nostalgic for the time Joey nuzzled Pacey’s English wool peacoat when the cast of Dawson’s Creek starred in a 1998 catalogue. Maybe you can’t shake the early imagery—when the seersucker was rumpled just-so, the chinos so sandy-kneed you could practically taste the sea salt, or, depending upon the season, the wood smoke. Today, scratch the surface of many a thirty- or fortysomething J. Crew fan (ahem) and you’ll find their inner teenager, waiting for the latest glossy dispatch from a land of just-beyond-reach privilege to arrive in the family mailbox. You couldn’t put your finger on it, exactly, but what these people had, you wanted.
This story has been updated.
