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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. 

Back at J.Crew’s offices, he staked out a separate space for editing what the Liquor Store would stock. (The name, and the original sign, were to stay put.) Only a handful of employees were allowed in. This was an exercise in precision. Mickey didn’t want too many voices muddying the vision. Between the various washes and fits, J.Crew produced some thirty different chinos. The Liquor Store would sell one. One kind of T-shirt, one kind of jean. The interior would feel clubby, almost cluttered, and dense with product—but the edit would be exceedingly clear. Men did not want too much information, Mickey said. The mantra: simplify.

In the back of the store, there would be a separate room for suits. Really, a suit. For the first time in decades—arguably since Mickey himself had helped foment the dereliction of taste known as “business casual” in the ’90s—young men had rediscovered the suit. On the flip side of the lumbersexual, we had smooth, suave Don Draper. Mad Men premiered in 2007, and suddenly skinny ties and charcoal-gray, slim-cut suits loomed large in the collective unconscious. Over on Planet Fashion, Thom Browne had pioneered the most radical reinvention of men’s tailoring since the leisure suit. This magazine dubbed him “the incredible suit-shrinking man.” Browne’s high-water tailoring freed the ankle, and even, for the extra-daring, the furry knee. These suits were both too fashion-forward and too pricey for the J.Crew guy, but their influence trickled down. Snyder knew the Liquor Store suit had to be lean, clean, and narrow. It also had to flatter the twenty-first-century mainstream American male who, sadly, bore little resemblance to Don Draper.

It took Snyder and fellow menswear designer Frank Muytjens two years to tweak the Ludlow Suit to perfection. In the end, it was deceptively simple looking: a skinny, two-button jacket and tapered trousers, which got its name after “the Tribeca” proved too difficult for J.Crew’s lawyers to trademark. What made it work so well “is still sort of a mystery,” admits Muytjens. “I’ve never seen a suit that fits so many body types off the rack.”

That one suit would more than double J.Crew’s tailoring business, becoming so ubiquitous that the New York Observer dubbed its followers “the Ludlow brotherhood.” In 2020, with J.Crew in distress, the Wall Street Journal mourned the maker of the single, $650 suit that changed the game for a generation of “fresh-faced 20-somethings wading into the workforce for the first time.” The Ludlow had became “a covetable commodity like a can of Coke or a pair of Nikes.” Can you think of another suit you know by name—other than perhaps Brooks Brothers’ No. 1 Sack Suit, the ur-suit of the twentieth century? Or of another one held its currency for more than a decade: in 2021, Prince Harry chose a pale gray Ludlow—princely, yet relatable!—for his and Meghan Markle’s fateful post-Megxit sit-down with Oprah.

Andy Spade had a theory about how to make a company like J.Crew feel cool: “the bigger you get, the smaller you act.” When the Liquor Store opened in August 2008, even the bottles of bourbon behind the bar were still intact. Old-timey bowling balls and oil paintings of toy dogs were strewn among the clothes. The speakers emitted the crackle of an old hi-fi. Spade’s own toy soldiers lined the mantel. There were stacks of books from the landmark bookseller the Strand, and even a mug of pencils prechewed by writers—this was somewhat less terrifying in a pre-COVID world, but still decidedly weird.

Over at Freemans Alley, the downtown Manhattan hangout that was the epicenter of the lumbersexual look J.Crew was unabashedly bogarting, owners Taavo Somer and William Tigertt—who by then had opened a clothing store of their own—were said to be less than thrilled. “They copied us down to the shade of the paint colors,” their sales director grumbled. But wasn’t that the ultimate compliment? Mickey had once launched a fleet of stores that were both inescapable, uniform down to the last crewsock, and instantly recognizable to any citizen of the Western world. Now he had one singular store that a man could stumble into, and have no clue he’d just entered J.Crew. Such was the evolution of the consumer that this was considered a victory. J.Crew might have been mass—inherently lame, from most tastemakers’ perspective—but it could code-switch at will to pass as small, indie, special.

The whole time the Liquor Store had been gestating, the board grumbled. Why the hell was Mickey wasting this much time and money on one microscopic store? But when it opened, none could deny its success. The Liquor Store never made a ton of money, but that wasn’t the point. It put J.Crew menswear on the fashion map. And provided a gold mine of data. Now they had granular detail on exactly what they were selling, and to whom. When size 36 suits started flying out, they knew they had tapped the elusive skinny style arbiter: suddenly, the J.Crew guy was giving the J.Crew girl a run for her money.

A month after the Liquor Store opened, Todd Snyder handed in his resignation; he was turning forty and was hankering to start his own company. Mickey was furious. “We’re on the launch pad,” he yelled. “We’re ready to take off! And you’re leaving?” Snyder has no regrets. Why would he? Today his brand is sold at that Liquor Store location, which he snapped up after J.Crew exited it during the company’s lengthy downturn. (The original neon sign still hangs outside.) Still, Snyder admits that none of them could see, at the time he jumped ship, that they’d just introduced the new uniform of the style-conscious American male. “I didn’t see how big this was going to be.”

Adapted from the book THE KINGDOM OF PREP: The Inside Story of the Rise and (Near) Fall of J.Crew by Maggie Bullock. Copyright © 2023 by Maggie Bullock. From Dey Street Books, an imprint of HarperCollins Publishers. Reprinted by permission.