According to Dickson, such moments helped remind people that Gap still exists. Since the company’s 1990s heyday, a combination of too many stores, too much merchandise, and a lack of cohesive vision had sent sales on a steady decline, and the company’s valuation from about $40 billion in 2000 to $8.41 billion in 2023, the year Dickson joined the company. He needed to capture attention quickly and improve morale. Posen’s creations for Hathaway, Erivo, and Da’Vine Joy Randolph at last year’s Met Gala did just that. “Those sparkles turned heads,” Dickson tells me, snapping his fingers. “The lights were now on at the Gap.” Though the cleanup began long before Posen’s arrival, Gap Inc. has seen sales grow for four consecutive quarters, and its stock is up 16 percent.
Posen, for his part, saw himself in Gap’s plight. “I love sleeping beauties,” he says, adding, “America loves heralding and shooting down. And I’ve definitely been a dove, a pigeon, a unicorn, and a dragon. So for me it’s like, What an opportunity!”
Back in 2019, after Posen’s company closed, he found himself in a professional abyss. He wondered how he would support himself. Posen went to Los Angeles, flirting with the idea of working in Hollywood. He tried Paris, where he interviewed for jobs at French houses. Eventually, he returned to New York, supporting himself with private commissions including bridal dresses, a piece for Drake’s 2023 tour, and costumes for Ryan Murphy’s Feud: Capote vs. The Swans. He and Dickson connected in the fall of 2023. Dickson was previously the CEO of Mattel, where he shepherded the Barbie blockbuster. “I’ve been a Willy Wonka at Mattel,” Posen recalls Dickson saying, “and I need to find my Willy for Gap.”
The company’s San Francisco headquarters has thousands of employees. Since I am also a child of the ’80s, the offices reminded me of The Sims, with its busy collective of perpetually smiling people, a “Gapeteria,” and a chief of technology named Sven. Posen bounds about its 15 floors, darting between meetings. To bypass the elevator bays, he’ll often just take the stairs. “I would be terrified to see my steps,” he says. He has joked that the company should get him a fireman’s pole so he can scoot down to his office.
The company’s language of corporate acronyms are a challenge for Posen’s dyslexia. His calendar is filled with SLT (senior leadership team) and LRP (long-range planning) meetings and reviews of P2Ms (product to market). For the first time in history, the company is redesigning stores for its brands all at once, and Posen goes over playlists, floor plans, and window displays. The day I visit marks the reopening of a Gap store in New York’s Flatiron neighborhood, and Posen proudly tells me that the paint on the walls was purchased with his personal Farrow & Ball discount. When he visited the new Banana Republic flagship in San Francisco, he inquired why the decor included a bowl of green apples and had it swapped out for an asparagus fern.
In the afternoon we settle into Posen’s office, where he unlaces his boots. “The shoes are coming off,” he says. “You don’t care, right?” It makes sense that Posen, who is highly tactile, would need to design barefoot. By this point in our time together, he had insisted on fixing the collar of my shirt, tried on a woman’s blazer worn by Gap Inc.’s VP of store development (who tells me that Posen inspected the fabric of her pants the previous week), unbuckled his pants to check the weave of a Gap tag, snapped a leaf off a plant to add to a mood board for summer, and studied the brand labels on denim worn by three separate Gap employees.
Posen slips a pincushion onto his forearm. He takes the corner of a denim sheet, pins it onto a mannequin just below the ribs, and tells me how, two weeks after meeting with Dickson, he flew west to appear before the company’s board. Their questions were what one might expect: What happened to his company? After making his name in eveningwear, why did he want to make jeans and T-shirts? Did he understand the complexities of a $15 billion business?
Posen had once led the way for a generation of designers that emerged in post-9/11 New York. His first show, which took place weeks after the towers fell, was made possible in part because the city’s factories emptied out, allowing his designs to be made. What followed was 20 years of ups and downs as he struggled to keep his business afloat, ultimately succumbing to the same forces plaguing many midsize fashion brands: a flawed wholesale model, the excesses of runway collections, and a lack of solid financial partnership to guide him through it all. The house’s intellectual property (including Posen’s name) has since been sold off to a licensing firm.