The designer Steven Alan is sitting in the basement of a Tribeca showroom, wearing a button-down from his own label—chalky gray, pin-striped, slightly rumpled. "Everything came out of the shirt," he says while rolling up a sleeve. "I think about different designers and how they developed, but for me there's this certain schoolboy sloppy look that I grew up with in the city. It's all in the context of New York," he adds, explaining the slouchy appeal of his now-signature wares.
Alan started out with a small boutique in SoHo in the mid-1990s. After searching vendors for a perfect low-key fitted shirt that seemingly didn't exist, he began working with nearby factories, cutting his own distinctly mussed varieties from washed cotton in muted stripes and plaids, with subtle details like exposed seams or interior breast pockets. The garments found favor among young to middle-aged urban guys who didn't want to look like, well, stuffed shirts, and Alan expanded with shorts, pants, outerwear, knits—a mini-empire that now encompasses almost 50 employees and three shops in New York, with L.A. locations set to open this year. This season also brings the first Steven Alan suits. Constructed in the Czech Republic out of durable wools—or in Hong Kong out of cotton—they are sharp for the price (around $700). And as if shuttling between production facilities and retail stores weren't challenge enough, Alan also runs SAS, the showroom he is presently sitting in, which represents some of the designers he helps discover and promote down the block at the Steven Alan Annex. (The Annex carries a variety of brands along with vintage eyewear and watches, while the remainder of Alan's stores now stock only Steven Alan originals.)
It's a sprawling business model that was not always a success, Alan admits. "Financially it was a mess," he says of his early days, when top buyers from Japan mounted a rickety staircase on Wooster Street to place orders. "We lost a lot of money. It was just the nature of representing all these small designers that were starting out and didn't have resources. We'd build them up, then they would go out of business, and it would keep happening until we found a happy medium of good designers that were financially sound, and new designers."
Alan, a divorced father who shares custody of his five-year-old son, keeps his head shaved clean. He is not a tall man; fit but not built. Though he boxes regularly, it's hard to imagine him intimidating a sparring opponent. And yet there is a drowsy charm to his gaze.
A growing fan base in L.A. led to the new branch on North Robertson Boulevard, an address firmly within the West Hollywood shopping district, but a breathable distance from that paparazzi stalking ground the Ivy. Gerry Beckley—folk-rock legend and founding member of America, a band that has miraculously been touring for 37 years straight—is one of Alan's most loyal West Coast clients. Beckley sought out the shop in New York years ago, met Alan, and the encounter led to a friendship. "I think there's a void in the market for a certain demographic of men who are a bit older," Alan says. "Gerry just looks right. He's got a good thing that fits him, and it works." A recent tour to promote Here & Now, America's first studio album in nine years, took Beckley from the Philippines to Singapore to India to New Zealand. "I travel about 200 days a year," he says, before enumerating the obvious demands that kind of schedule places on one's wardrobe. Beckley praises Alan's clothes for their "wonderful consistent quality." On the road, he mixes them with gear from A.P.C. and Engineered Garments, as well as Alden shoes made specifically for him. "I like classic things," says the man who wrote "Sister Golden Hair" and "I Need You": "Steven's work has a certain quality to it. It doesn't yell."
