On today’s episode of The Run-Through, Chloe invites Vogue’s Virginia Smith to break down how the top-secret May cover—featuring Meryl Streep and Anna Wintour—came to be. You’ll also hear snippets from Greta Gerwig’s conversation with the two women, as they discuss aging, grandmotherhood, and which part of each other’s job they would dread the most!

But first, Rachel Comey speaks to Nicole Phelps about her unconventional origin story, how she funded her brand in the eary days, and the upcoming opening of her Christopher Street store. She also discusses how she managed to stay independent and find her own audience—one that has come to include writers, directors, and artists like Zadie Smith and Miranda July.

Of her design process, Comey says, “I really think about design as a service to the client and making sure that they’re feeling the things they want to feel in the rooms that they want to go into.” As fashion slowly catches up to the inclusive casting Comey has long practiced, she plans to keep doing things her own way.