Dorothy

Touring the remodeled Gap flagship store in Manhattan’s Flatiron District during an interview for Fortune’s Behind the Business video series, Dickson paused beneath framed photographs by Annie Leibovitz and Bruce Weber showing Debbie Harry, Willie Nelson, and Lauren Hutton sporting Gap’s classic American casualwear. Nearby are huge photos of Hailey Bieber, a “Gap girl” of today, promoting her new denim line with the brand.

The juxtaposition illustrates the strategy that Dickson—who became CEO in 2023 after a tumultuous stretch in which Gap Inc. cycled through five CEOs in five years—is pursuing. He’s trying to reconnect the company’s namesake chain with the cultural conversation. That’s why he brought in the designer Zac Posen as Gap Inc.’s creative director and Old Navy’s chief creative officer, invested in celebrity collaborations, and leaned into the company’s history.

The early results are encouraging. Gap comparable sales rose 10% in the first quarter, extending a two-year streak of growth. Its “Better in Denim” campaign with global girl group Katseye generated a viral Busby Berkeley-style dance number that has been viewed 80 million times, while a limited-edition hoodie collaboration sold briskly. Victoria Beckham, Malcolm Todd, and Inde Navarrette have also joined the effort, while Old Navy is working with Cardi B on denim.

Riding a wave? Despite the green shoots, Gap Inc’s shares are down 20% this year and have been largely flat since they soared right after Dickson’s appointment in 2023. His turnaround plan is very much still a “show-me” story, according to Simeon Siegel, an analyst with Guggenheim Partners. For one thing, many apparel retailers have seen sales growth this year, but much of that was just higher prices they could pin on tariffs and broader inflation. Siegel says the real test is whether Gap can raise prices because people really want its t-shirts and jeans.

Dickson knows a thing or two about culture’s potential to transform a brand. Before Gap Inc., he had been at Mattel since 2014. There, his achievements included revitalizing the “Barbie” brand and putting it back at the center of popular culture with creative marketing campaigns. His work helped set Barbie up for the enormous success of the blockbuster 2023 movie based on the doll.