Derek Guy is the editor of Put This On, a blog about dressing like a grown-up. He also runs his own men’s style site, Die, Workwear.

In 2008, as Vampire Weekend was crooning about Cape Cod and Pete Campbell wore tennis sweaters on “Mad Men,” J. Crew was gearing up to open its much-anticipated Liquor Store in Lower Manhattan, an after-hours watering hole transformed into a menswear-only boutique.

The store’s designers draped cashmere cardigans over leather armchairs, arranged Alden brogues next to Globe-Trotter suitcases and hung rep striped ties across the railing of a bar. A bookshelf full of Kerouac, Cheever and Hemingway lured in men yearning for a stylized past.

Times change. And on Monday, the company announced its filing for Chapter 11 bankruptcy protection. But even as J. Crew struggles to turn a profit, men who are trying to build a better wardrobe very much need companies like it. J. Crew served as a bellwether for American men’s style — not necessarily setting the trends so much as confirming them. In doing so, J. Crew helped men dress better without trying too hard.

Founded in 1947 as Popular Merchandise before rebranding as J. Crew in 1983, the company sold preppy-with-a-twist products through their colorful, aspirational catalogues for much of the 1980s and ’90s before exploding in popularity in the early 2000s. In recent years, however, the company has been bogged down with flagging sales, quality-control complaints and a $1.7 billion debt load stemming from a 2011 leveraged buyout. The retail shutdown caused by the coronavirus pandemic seems to have been the last straw.

J. Crew didn’t start the heritage menswear movement that defined men’s fashion during the late aughts, but it was its most visible mass-market retailer. By framing cotton button-downs and chinos in the context of throwback masculinity, J. Crew made them seem more interesting and less utilitarian than the cotton button-downs and chinos in the stores on the other side of the mall concourse. The company struck a happy medium: less staid than Brooks Brothers, with more flavor than the Gap. It was more relatable than Dior but not a caricature like Abercrombie & Fitch. Most of all, it provided all its “elevated" basics under one roof and at affordable, mid-tier prices.

For millions of men, it was at a J. Crew store where they first got to handle chin-strapped chambray shirts, spongy Fair Isle knits and heritage brands such as Barbour and Baracuta. By telling the history behind materials such as madras — a once-rare fabric made famous in the 1960s by Brooks Brothers — J. Crew helped make classic American clothing feel relevant to a younger generation.

J. Crew lowered the barriers of entry and made a higher-quality wardrobe accessible. It used a relatable design language and told stories about clothes that inspired confidence and made dressing well something to aspire to. The once-innovative, now-cliche J. Crew pieces — the gingham shirt; slimmer-fitting, flat-front chinos; narrow-lapel suit — became the professional guy’s uniform because they made guys look better.

Today, consumers who shop for value have more options than ever. There are now thousands of digitally native brands that specialize in just one kind of item: UntuckIt has branded itself around short-hem shirts; Gustin has built a business around affordable raw denim jeans. And as J. Crew has faded, the middle of the market is getting squeezed by luxury brands and fast-fashion retailers. Mid-tier companies such as J. Crew and Banana Republic don’t have the uniqueness of the first or the price-competitiveness of the second.

If you want to dress in head-to-toe Gucci — or H&M — you still have stores for that. But for men who want something classic, generally appropriate, well-made at a reasonable price, you may soon have to scour the Internet for the best makers of socks, then chinos and then shirts. Then, you’ll have to figure out yourself how to combine these things into a coherent outfit, rather than rely on dedicated sales associates who know the story behind each piece — the sort of person who worked at, say, J. Crew.

In some ways, fashion has developed along the same trajectory as television. Back when everyone had cable, you could discover things without looking too hard. Because everyone relied on the same small number of networks, the best shows continually popped up in conversation. Today, the Internet has made possible a near-infinite number of streaming services. There’s more niche programming, but you have to pay closer attention to know what to watch.

Today it’s unclear whether J. Crew will be able to find a way forward. The company has lost most of its cultural capital, it’s saddled with $1.7 billion in debt, and it has trained customers to shop on sale with near-constant promotional codes. But many men would still benefit from having a J. Crew — or something like it — nearby.

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