The Shirt That Ate Manhattan

Steven Alan reinvented the button-down for artfully rumpled hipsters.

By Amy Larocca

In 1999, Steven Alan designed the perfect shirt. He did this not by reinventing the essence of shirtness but by tweaking it—very, very precisely. Alan started with a traditional button-down shape, bought up rolls of “jobbers” fabric—traditional checks and stripes—and then he went to town on the details.

His shirt had to be fussy in its tailoring yet unfussy in its final effect. Short enough to hang just right over pants but rumpled enough to distinguish its wearer from the desk-job grind. Unstudied, yet a perfect fit. Alan himself sums it up by saying, “I didn’t want it to look”—and here he’s careful to specify—“European.”

It took a while to get it right. Alan had to educate himself in the business of production: “We went through five or six factories in two years before we found one that was right,” he says. “We have up to 75 patterns, stripes and plaids and checks, which makes it difficult to match the fabrics. There’s tons of room for error.” Then the shirts go to various wash-houses, including ones that distress jeans, for a softening bath. After all the fine-tuning, Alan had captured the self-conscious “this old thing?” look that a generation of Spike Jonze–admiring, cool-sneaker-collecting guys wanted.

Steven Alan is now producing 1,000 shirts each week, enough that he has to be careful to retire fabrics that become too popular. “I never want to make too much of any one thing,” he explains. Demand at his shops in Tribeca and on Amsterdam Avenue, as well as at the various stores to which he sells wholesale, including Barneys New York, has grown consistently. In some California stores, the shirts rarely make it to the shop floor, they’re gobbled up so quickly by advance orders and wait lists. They’ve achieved a cult status, like those classics with which they look best: well-worn Levi’s cords and a beat-up pair of Chucks.

Now Alan is meeting all this demand with abundant supply at the Steven Alan Annex, a tiny shop on a deliriously trendy corner of Nolita (229 Elizabeth St., nr. Prince St.; 212-226-7482). It’s devoted almost exclusively to shirts cut for both men and women—who, it turns out, like the idea of looking sexy in a borrowed boyfriend shirt, particularly if it’s not actually borrowed and fits just right. There are also a few cashmere sweaters, Italian Army sneakers, vintage Rolex watches, and, Alan says, “whatever I realize I need,” which right now takes the shape of washable corduroy overcoats and the occasional pair of flat-front pants.

But the shirts take center stage: They’re piled to the ceiling in a dizzying mass of stacks whose artful messiness itself is another manifestation of Alan’s aesthetic.

The piles probably won’t stay high for long. For thirtysomething New Yorkers weaned on Beastie Boys and late nights at the Cherry Tavern, Steven Alan shirts are the finishing touch on an ideal look: preppy spiked with very calculated sloppy and just a little touch of street. “Refined,” as Alan says, “but disheveled.”