J.Crew Survived Bankruptcy. Next Up: Cultural Relevance?

“Guys, I want a little bit more dimensionality,” Libby Wadle says as she eyes a mock-up for J.Crew’s fall store displays. The setup being workshopped at the company’s headquarters on the southern tip of Manhattan drips with soft maroons and a bracing chartreuse—the color of Wadle’s own organza wrap skirt—that reads like the cool older sister to last year’s ubiquitous Brat green. Her solution: The arrangement could benefit from a print. “Something that’s a little bit more dynamic up front,” Wadle instructs the buzzing design team before hustling to the adjacent studio of sister brand Madewell, differentiated in part by the Madewell consumer’s preference for creamy ivory denim—ecru, for the initiated—versus a J.Crew shopper’s white jeans.

The 52-year-old chief executive officer has been at J.Crew Group LLC—corporate parent of J.Crew, J.Crew Factory and Madewell—long enough to know what makes a successful back-to-school display. She’s worked here for 21 years (nearly five as CEO) and before that, almost a decade at Gap Inc. Many of those were under the tutelage of legendary Gap CEO Mickey Drexler, who later recruited Wadle to J.Crew during what would eventually become the company’s 2010s heyday, when Michelle Obama’s sprinkling of J.Crew pieces into her first-lady wardrobe helped push the brand to the cultural forefront. “I think the Obama moment was probably the top of the top,” Wadle says. It’s the kind of relevance she has in her sights for J.Crew once again.