Back in the 2010s, J.Crew’s former leading lady, Jenna Lyons, was one of fashion’s biggest trendsetters, making thick eyeglasses, high-low style combos, bedazzled sweaters, and a cuffed button-down some of the decade’s must-haves. For years, her style represented J.Crew’s point of view for fashion fans, who looked to the brand’s leader for inspiration. Still, for all the fame Lyons earned during her tenure at J.Crew, the designer wasn’t as quick to adapt to the rise of Instagram’s designer-customer relationship, only joining the app in 2020, after she had left the company. While J.Crew enjoyed a good run as one of America’s favorite brands for years, by the mid-2010s, it became just another casualty of millennials’ appetite for increasingly digital brands and authentic connections and aversion to all things cookie-cutter… or found in a mall.