I do love a hoodie,” Questlove says, stepping into the Hoodie Shop on Orchard Street from a light afternoon rain. The Roots drummer and Late Night With Jimmy Fallon bandleader (real name: Ahmir Thompson) is an old friend of the shop’s co-founder, Peter Shapiro, who owns the Brooklyn Bowl, where Quest spins on Thursdays. Soon he’ll D.J. here, too—there’s even a booth built to suit him. “I have a love affair with hoodies that goes way back,” he continues, checking the price tag on a plain yellow option. “When Tariq [Trotter, the Roots’ M.C.] and I first saw the Tribe Called Quest video for ‘Can I Kick It?’ and they were all wearing hoodies, I was like, ‘Yo, we gotta go to the Gap and get that.’ That’s when I purchased my first bona fide hoodie.”