In 2012, Meghan O’Neill, a writer and comedian, started an online video-collage series called “J. Crew Crew.” Each video was made entirely with images taken from the J. Crew catalogue and followed the J. Crew Crew as it voyaged into a world of surreal intrigue and mystery. In one episode, a willowy detective in a tweed jacket and Ray-Bans travelled to an island wedding, where she attempted to solve a murder with the help of two child ghosts (girls dressed in J. Crew’s kids line, Crewcuts); in another, a woman in a white linen shirt was abducted into a cult in which everyone wears jewel-toned special-occasion dresses. “J. Crew Crew” made fun of the bizarre alternative reality conjured by J. Crew’s catalogues, in which children and adults dressed exactly alike, Jackie O. and Helena Bonham Carter had combined their closets, and faux-quirky mean girls shared an unlikely, touchy-feely bonhomie. It was funny because it acknowledged how attractive that reality could be.

Few brands have imagined their worlds as completely as J. Crew. From the eighties onward, the company’s “style guides” were really life-style guides; they mapped the hours and days of a certain kind of charmed existence, showing how a recent college grad with a creative-professional job might dress for brunch, work, a date, a hike, a vacation, or a wedding. When the last full installment of “J. Crew Crew” appeared, in 2014, that vision was still appealing. J. Crew exercised an unparallelled influence over the way affluent Americans dressed, especially at work; Michelle Obama wore J. Crew during state visits to Turkey and the U.K. It’s startling to realize that, by then, the company was already beginning its decline. Sales at J. Crew have fallen for two years. The company is two billion dollars in debt, putting it in danger of bankruptcy. A few months ago, J. Crew shuttered its bridal business; earlier this month, Jenna Lyons, its president and creative director, announced that she would be stepping down; and, last week, J. Crew laid off a hundred and fifty employees and eliminated a hundred open positions. (Frank Muytjens, its head of menswear, is also leaving.) In an attempt to boost revenue, the company has started selling its clothes through Nordstrom. In 2010, when Nick Paumgarten profiled Mickey Drexler, J. Crew’s C.E.O., for this magazine, none of this was imaginable. What happened?

Part of the answer has to do with design. In the mid-aughts, J. Crew cracked the code of all-day dressing for the “creative class” by combining the formal with the informal: it sold tuxedo jackets you could wear to the office and sequined blouses that could work under military jackets. Today, the sensible version of the Jenna Lyons uniform—nerdy glasses, nice blazer, lived-in jeans, heels or sneakers—is omnipresent. Over time, however, J. Crew’s designs grew overpriced, eccentric, and even downright ugly. As one J. Crew blogger put it, in a post called “Do You Still Heart J. Crew?,” the company seemed to be “catering to the fashion editors and fashionistas from Fashion Week more than the base of loyal aficionadas”; it tried to create a daring, post-prep aesthetic and overreached. There were quality-control problems, too, and missteps with fit.

And yet J. Crew has also faced fundamental problems beyond its control. Earlier this year, in an article for the magazine The Business of Fashion, Chantal Fernandez explained why “America’s most beloved mall brands”—J. Crew, Gap, The Limited, and Abercrombie & Fitch—are all in crisis. (The Limited filed for Chapter 11 in January, and has closed all of its stores.) The short answer is the Internet. Millennials tend to spend money on gadgets, rather than clothes, and rarely go to the mall; savvier customers have learned to wait for coupon codes. The middle of the market has disappeared: while aimless, open-minded shoppers are happy to haunt Zara and H & M, discerning ones turn every purchase into a research project, gravitating toward Web-centric brands such as the California fashion startups Reformation and Everlane, which are more transparent about sizing and manufacturing. Then there is Amazon, which accounts, by itself, for more than half of all growth in online retail, according to the market-research company Slice Intelligence. By allowing customers to search across brands, it devalues branding in general, reducing the potency of the world-building in which companies like J. Crew have invested so much.

When I recently dropped into the J. Crew store near my office, it was easy to see how all of these problems had converged. The environment was pleasant, and the salespeople courteous, but the clothes had looked better online, where they appeared on models, than they did on the racks. (It’s unfair to fault them for existing in physical reality, but that’s 2017 for you.) The store was typically sized, but the selection seemed oddly small—smaller, at any rate, than the selection offered by the entire Internet. In the women’s section, the spring collection offered seersucker dresses with extravagant evening details, such as ruffles and bows. The collection has been hyped as a return to form—Vogue praised its “zeitgeisty” and “zhuzzed-up approach to daywear.” (“In the era of Instagram, isn’t every day a red-carpet event, a photo opportunity?”) When I contemplated those dresses, what struck me was their willful nostalgia; preppy clothes may be inherently nostalgic, but the whimsy of these items seemed over the top. During the Obama years, nostalgia might have seemed harmless, even admirable, but today it feels like a troubled and doubtful impulse. Does it make sense for young, urban men to dress up like Rust Belt factory workers, or for women to embrace the style of Hyannis Port in the nineteen-sixties? The answers to those questions have changed over the past six months.

The most striking thing about the store was, for lack of a better term, its pervasive, all-encompassing J. Crewness. Every item—critter shorts, pocket squares, the Frankie sunglasses—represented a facet of a familiar, imagined life. The names of the products—the Ludlow and Crosby jackets for men; the Rhodes and Maddie pants and Campbell and Regent blazers for women—fixed J. Crew in a certain place and milieu. Once, this was comforting. Now it felt odd to be told by a company that I was, or wanted to be, a certain kind of person. I didn’t want to be a member of the J. Crew Crew, or any crew.

Later the same day, I logged onto Facebook. My newsfeed was, as usual, full of ads for streamlined, nondescript clothing that might be described as “normcore”: sneakers from Allbirds, T-shirts from Buck Mason, crowdfunded trousers from Taylor Stitch. A few friends, I noticed, “liked” Bonobos. The ads rejected, or claimed to reject, the whole idea of “life style.” In many cases, they showed products without models, just floating in space. The implication was that I was a self-defining, self-sufficient person. I didn’t need to aspire to some other life; I could build one myself, without entering some bubble-like subculture. In theory, these clothes said almost nothing about me. (In practice, of course, they say as much as clothes always do.) It’s this insistence upon independence that, more than anything, may have dethroned J. Crew. These days, we prefer the subtle manipulation of the algorithm to the overt glamour of the “style guide.” It’s luxurious to think that we are choosing for ourselves.