For Questlove, it was also important to incorporate the sharp silhouettes that he grew up seeing worn within his own family. His father, the notable soul singer Lee Andrews, served as the leader of Lee Andrews & the Hearts for years—and was a prolific suit wearer himself. “There was a portion of my dad’s life in which he wore nothing but suits—for decades, even in summer,” says Questlove. Some of the artist’s earliest memories involve seeing his father suit up. “As a way to keep an eye on me when we were touring, my father made my job in show business taking care of his wardrobe,” says Questlove. “I was seven—running his clothes to the dry cleaners, steaming the suits, his shoes and his accessories.” For a finishing touch, the star added jewelry by Brooklyn-based artists Bernard James and Burkindy from Burkina Faso, as well as Ferragamo shoes.

Lee Andrews & the Hearts

Photo: Courtesy of Questlove

He and Hearst kept those memories in mind, and were inspired to create a suit with a more elongated, double-breasted shape in his honor—and the use of pearls also gave it an unexpected, fresh feel. They also cited references such as pinstripe suits worn by Sammy Davis Jr. and Duke Ellington. “We thought about Black dandyism in relationship to Black men in music,” says Hearst. For Questlove, the spirit made for the perfect end result. “Coming from a family of uncles and a dad who wore nothing but tailored zoot suits in the 1950s and 1960s—I used to make fun of their photos hanging in my grandma’s house all the time—the irony isn’t lost on me that now I get to follow in their footsteps and having fun while doing it,” he says.

Though last night wasn’t Questlove’s first Met Gala, the star adds that there was indeed a special mood in the air at the Met. It was also a full-circle fashion moment for him on the red carpet, given there was a time in his life when he would never even be caught in a formal suit. “Because my dad’s generation was so gung-ho on ‘respectability politics,’ I eschewed suits like the plague,” he says. “And then The Tonight Show came, and suits are in my vocabulary. My first month on the show, Prince was so impressed with my mohair double-breasted first suit that he tipped me $50 just for looking ‘so damn clean.’” It’s hard to top such a moment, but tonight’s Met Gala was a close runner-up. Of his memorable outfit, he says, “I wish my photo could hang in my grandmother’s house back in the 1970s.”