Richard Dickson had an advantage, this past July, when he was named C.E.O. of Gap Inc. the company that owns Gap, Banana Republic, Old Navy, and Athleta. Unlike most C.E.O.s, who spend their first 90 days just trying to understand what exactly they’ve gotten themselves into, Dickson had already been a member of the board since November 2022, eight months earlier, which gave him special insight into the company’s challenges, and, some would say, opportunities. 

Dickson, who spent most of his career at Mattel, recently received a lot of credit for the commercial success of brand collaborations connected to Barbie. Now, he’s managing a far more complicated portfolio. Gap, the namesake brand, remains the most alluring to consumers. Despite its perpetual discounting, and its lack of necessity in these times, people remain nostalgic for the days when it was the biggest brand in middle-class America. 

For better or worse, Casual Friday wouldn’t have happened without the Gap (or Mickey Drexler, the merchant prince and chief brand architect in its heyday). Drexler permanently changed the way people dressed, and we continue to fetishize the glamorous, not-too-sloppy version of that informal look: a starchy white shirt, tucked into great-fitting jeans, cinched with a stylish belt.