Good morning. Phil Wahba writing this morning from New York. Gap Inc. CEO Richard Dickson has a theory: A brand cannot sell its way out of irrelevance.
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.
“We had great storytelling and brands, but somewhere along the way, we lost the story and became more about the stuff,” Dickson told me. “Cultural connection and relevance actually are a fundamental part of brand management.”









