When How to Dress Well’s music first surfaced in 2009, it wasn’t exactly clear what it was or how to classify it: Intimate yet remote, immediate but murky, it felt like a lost and forgotten cassette of ’90s R&B. The work of singer-songwriter/bedroom producer Tom Krell (born in Boulder, Colorado, in 1984), HTDW’s sound became a bellwether for the 2010s, giving pop a distinctly un-pop feel in ways that came to permeate both the underground (FKA twigs, James Blake) and the mainstream (Frank Ocean, The Weeknd). Krell’s subsequent albums (2012’s u003ciu003eTotal Lossu003c/iu003e, 2014’s u003ciu003e“What Is This Heart?”u003c/iu003e) were increasingly direct and vulnerable, bringing his falsetto into the light while retaining an air of mystery that made his early recordings so unusual. (That Krell was also working on a doctorate degree in German philosophy didn’t hurt: He didn’t just have feelings, but he had ideas about feelings too.) Coproduced by Jack Antonoff (Fun., Lorde, Taylor Swift), 2016’s u003ciu003eCareu003c/iu003e made a full-on stab at pop—a move Krell described as “a wager.” Reflecting on the album, Krell tells Apple Music that “to do something not-transgressive was very transgressive to me.” Dark, fragile, and noisy, 2018’s u003ciu003eThe Anteroomu003c/iu003e is everything its predecessor wasn’t—what Krell describes as u003ciu003eCareu003c/iu003e’s “evil twin.” For Krell, the unifying goal is simple: “To make something really beautiful.” Reflecting on the ground covered during the first decade of his career, and the creative shifts that took him from u003ciu003eLove Remainsu003c/iu003e to u003ciu003eThe Anteroomu003c/iu003e, he confesses, “I don’t know who I am—and that’s my aesthetic as well.”