As Gap Inc. CEO Richard Dickson gives us a tour of the Gap’s remodeled store in New York’s Flatiron District, he pauses at a gallery of 16 framed sepia-toned pictures hanging above a staircase: work by legendary photographers Annie Leibovitz and Bruce Weber, capturing celebrities from musicians Debbie Harry to Willie Nelson to actress Lauren Hutton for long-ago ad campaigns.
He found the photos—and hundreds more—in the company’s archives soon after taking the helm of the brand’s parent company in 2023, Dickson said. They recalled a time when the Gap was firmly at the center of pop culture, and he thought they should be on display in the flagship store—a few yards away from gigantic posters of contemporary “Gap girl,” the influencer and cosmetics entrepreneur Hailey Bieber, who has launched a new jeans line with the Gap.
Since the very beginning of his tenure, Dickson has put restoring the “cultural relevance” of the Gap, along with sister brands Banana Republic, Old Navy and Athleta, at the very top of his agenda, alongside the more prosaic priorities for a clothing brand: quality, well-appointed stores and supply chain prowess. One of his early moves as CEO was to hire designer Zac Posen to be creative director of Gap Inc. and chief creative officer of Old Navy.
