BoF’s Cathaleen Chen and Marc Bain join Lauren Sherman to talk about retailers’ big hires, hopes and plans for bringing their brands back to life.   Background:      J.Crew and Gap defined how Americans dressed for much of the ’90s and 2000s, until their clothes grew stale, malls emptied out and fast fashion took retail’s reins. Then, during the pandemic, J.Crew filed for bankruptcy and Gap closed hundreds of stores. More recently, they’ve both orchestrated attempts to win back consumers: Gap, with its Yeezy-Gap collaboration, and J.Crew, with new mainline designers, including former Supreme creative director and Noah-founder Brendon Babenzien, whose menswear collection dropped a few weeks ago.    Though they share similar histories, the retailers’ comeback plans couldn’t be any more different.    “[Fashion] is a challenging business because people love it but to actually make money in it is not the easiest thing in the world… It takes a lot of ruthlessness and difficult decision making,” said Lauren Sherman, BoF chief correspondent.      Key Insights:      In the late-aughts, CEO Mickey Drexler and designer Jenna Lyons turned J.Crew  into a fashion powerhouse before insurmountable debt sent it into bankruptcy a few years later. Meanwhile, Gap struggled to define its design aesthetic after dominating 1990s mall fashion with its preppy basics.  With its 2020 appointment of the artist then known as Kanye West, Gap has been able to generate hype, but not sustained sales. Yeezy Gap and Gap are still mostly bifurcated: its retail rollout in Times Square featured clothes in black trash bags, in a blacked-out room separate from the rest of the Gap store. Gap has a mostly mass-market customer — begging the question of whether Yeezy Gap, even if better integrated into its model, is the right fit.  Under former Madewell chief Libby Wadle’s leadership, J.Crew has restructured and tapped two sharp designers to home in on its heritage while edging it up and playing with trends. Babenzian released his first collection in late July, which generated a ton of buzz on social media.  Both retailers face significant headwinds, but J.Crew is best poised to win given its balanced merchandising strategy aimed at satisfying new and old customers, said retail correspondent Cathaleen Chen. Particularly tough, added technology correspondent Marc Bain, is the fact that Gap is so large, and beholden to shareholders.     Additional Resources:      J.Crew’s and Gap’s Comeback Playbooks Couldn’t Be More Different. Only One Is Working: After the pandemic, the American retailers hired big fashion names to breathe life into their brands. But as the collections released this week show, the similarities end there. The J.Crew Comeback Starts Now: With its new menswear collection under creative director Brendon Babenzien, the retailer has its best shot in years at returning to the fashion zeitgeist. Yeezy Gap Brings a Dystopian Retail Experience to Stores: Clothes from the collaboration between Gap and Ye (formerly Kanye West) went on sale in a physical Gap store for the first time today, in a blacked out space where clothes were piled into plastic bags.     Follow The Debrief wherever you listen to podcasts.