“The Bigger You Get, the Smaller You Act”: How a Downtown Liquor Store Supercharged J.Crew’s Menswear Boom

In The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew, Maggie Bullock explores the rollercoaster life of the iconic American brand—including the enormous success it found selling clothes out of a converted liquor store in Tribeca. 

Mickey Drexler was a born shopkeeper. The C.E.O of J.Crew from 2003 to 2017, he ran a massive American retailer like a merchant behind the counter of his own mom-n-pop, quizzing his customers face-to-face, forever juiced by the energy of the sales floor. To him, stores were the whole point. So around 2007, he was irked. At his bidding, J.Crew had executed a complete 180 on its peppy, preppy navy-blue-blazer menswear look. Mickey was betting big on the “lumbersexual” look of the day—dark, cuffed denim; “heritage” Red Wings. Yet he did not have a shop in which to feature it.  Sure, most J.Crew stores carried men’s clothes, but womenswear—the cash cow that accounted for some 80 percent of their sales—got pride of place. The men’s department got the dregs, hidden away downstairs or tucked in the back. 

What was the point of having a newsworthy new look if you didn’t have a proper boutique where it could all come together—where customers could see it in context, soak in the sum of its parts? But according to Todd Snyder, Mickey’s head menswear designer (whose eponymous brand, as readers well know, is now one of the great menswear success stories of the 2020s) the board of J.Crew kept talking Mickey down. They knew their resident “merchant prince” could get carried away. Keep your eye on the ball, they told him. For a while, he listened.

When Mickey could stand it no more, he asked branding expert Andy Spade to drop by the office. Spade is the cofounder, with his late wife, Kate Spade, of the brand that bears her name, as well as the men’s accessory range Jack Spade. He’s also, like Mickey, a natural born stores guy, master of the immersive shopping experience. Mickey surely knew what he would get from Andy Spade, who as expected took one look at J.Crew’s new array of reinvented menswear and announced, “You gotta have a store!” 

“I knew it!” Mickey crowed. 

That very day, Spade took Mickey and Snyder on a field trip. He knew just the spot, he said: a tiny, grimy out-of-work bar on a crooked corner in Tribeca. The original bar was still intact, down to the bourbon bottles, and the little neon sign in the window: Liquor Store. Even the old cash register was still there. “It was a no-brainer,” Snyder says.

Courtesy of Dey Street Books

In a former life, Mickey had been the explosive force behind the ‘80s and ‘90s rise of Gap, Inc. He  grew Banana Republic (acquired by Gap in 1983) into a household name. Invented Old Navy—the baby that quickly left its older siblings in the dust—from scratch. At the helm of those three companies, he once opened a new store in America every single day. But in 2007, running the very different beast that was J.Crew, Mickey spent months carefully honing the concept of a single, nine-hundred-square-foot shoebox. 

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