Posen’s hiring came at a moment when both he and the Gap stood to benefit from a reinvention. In the nineties, under the C.E.O. Mickey Drexler, the Gap was considered the go-to outfit of the stylish Everyperson. Ubiquitous TV commercials featuring young people swing dancing in khakis or lip-synching to “Mellow Yellow” gave the brand a sheen of fresh-faced relevance. Gap print ads were shot by Annie Leibovitz and Herb Ritts. The “Friends” cast wore the Gap. Sharon Stone wore Gap tops to the Oscars—twice. But sales peaked in 2000, and in 2002, after a seventeen-year tenure, Drexler was fired amid slumping profits. He went on to revitalize J. Crew. Gap Inc., meanwhile, struggled to adapt to a retail landscape increasingly dominated by e-commerce and fast-fashion competitors such as H&M and Uniqlo.