“The PRs told me, you cannot leave Manhattan, and you can’t do a dinner—people are too busy,” recalls Comey of her decision, in 2013, to scrap her catwalk show in favor of an intimate supper-club-style presentation in Brooklyn’s difficult-to-reach Red Hook neighborhood. A seat at a Rachel Comey dinner—replete with cabaret courtesy of Justin Vivian Bond, or Tracee Ellis Ross on emcee duties—became a coveted invite, and not only for fashion insiders: You might find yourself seated across the table from Cindy Sherman, or Debbie Harry, or Maggie Gyllenhaal, or Zadie Smith. “We can get so siloed off—fashion over here, writers over there—I thought it would be interesting to let people mingle,” Comey explains. Some guests were pals; others, she confesses, were artists whom she admired and simply cold-called, operating on the principle that if you feel connected to someone’s work, chances are the regard is returned. Smith, for one, attests to this: “When I get dressed, my first priority is not to look sexy or pretty or skinny or young—I want to look cool,” she says. “And to me, Rachel’s clothes are a shortcut to that. They’re clothes for me to enjoy.”

Women who design for women: They get dinged for being too practical, too focused on stuff like pockets to conjure any fantasy. Rachel Comey, the brand, rebuts this claim. Not that Comey, the designer, doesn’t prioritize functionality. One reason she sees the 2014 opening of her first store, in Manhattan’s SoHo, as such a milestone is that it allowed her to better comprehend her clientele. “Seeing customers shopping in real-time, getting the sales reports…. It was like, mind blown,” she says. “Who is she? Where is she going? What is she doing? What does she need? How do I problem-solve for that—if she has to give a speech, and she’s standing a long time—what are those shoes?”

“But at the same time, I was also putting the pieces together in terms of where I wanted to go with the aesthetic,” Comey continues. “Part of my job, on top of the problem-solving, is to offer propositions that are surprising and delightful—a sharper shoulder, or a fabric that’s a little bit of a challenge—it’s ‘off’ in some way. Try this.”