How to Dress Well’s Tom Krell is an enigma

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Figuring out what’s fact and what’s fiction can be tricky when it comes to the work of How to Dress Well’s Tom Krell. The singer has stated that no one can hope to know him through his songs, something that seems strange considering how much of his private life appears to filter into his records.

Take, for example, 2012’s Total Loss, a release that he’s candidly admitted was coloured by depression, death, and the despair that comes with such bleakness. Or consider the leadoff track, “2 Years On (Shame Dream)”, from his game-changing new album, “What Is This Heart?”. The song’s lyrics (“There’s no (de)sign, no God/Just the future and my mother’s broken heart”) take on a powerful new meaning once you know something about Krell’s family history

The mother of the Chicago-based singer, songwriter, and multi-instrumentalist has suffered from depression to the point where it’s had a major impact on those around her. The family tribulations don’t stop there. Krell’s older brothers have Asperger’s, making it difficult to form the kind of bonds that most siblings enjoy.

Once you know such details, you can look at “2 Years On (Shame Dream)” in a new light, especially when it comes to lines like “He knew they were men, he knew they were no different than you or me or any other guy/Yet he knew that they were never just all right.” The same goes for “No one ever told you life would be this unfair—oh, it is/No one would ask this for themselves.”

Don’t, however, suggest to Krell that you’ve somehow just discovered a window into his private life by carefully analyzing the songs on “What Is This Heart?”. In fact, float the idea that he’s something of an enigma, and he happily agrees.

“I’m happy to hear you say that,” the singer says, on the line from the Windy City. “People are always like, ‘Your music is so personal that I know all about you.’ And I’m like, ‘Oh yeah—what do you think that you know about me?’ What does one think that they can glean just straight away from a song? It does take some work, and everything is quite enigmatic. But that’s the appeal for me. I hate the idea that people think that I’m sort of an open book, when really that’s so false.”

That reluctance to pull back the curtain might explain why Krell is friendly but guarded as an interview subject. The man known as How to Dress Well is at times open, at times prone to talk in circles, and sometimes just plain difficult to crack.

There’s a case to be made, for example, that the singer didn’t completely exorcise his demons with Total Loss, a downtempo R&B record that hit big with critics. (To give you a sense of when work started on “What Is This Heart?”, Krell was already talking about the project in interviews while doing early promo for Total Loss.) He shoots that theory down, noting instead that he’s one of those guys who, rather than sit there and admire what they’ve done, are more interested in keeping busy.

“I’m always writing new music, so it’s not like ‘I didn’t exhaust my message, so I must go back to the grindstone and get my message out,’ ” he says. “It’s more like ‘I have 20 minutes—maybe I’ll write a song.’ ”

Krell also argues that “What Is This Heart?” didn’t have him making a conscious attempt to reinvent himself as an artist. Up until this point in his career—and to his chagrin—he’s been lumped into an indie-oriented R & B movement that’s given us the likes of Frank Ocean and the Weeknd. (This has led to his being saddled with tags like the admittedly clever “PBR&B”.)

The modern-soul-man vibe has been toned down on “What Is This Heart?”. Instead, Krell laboured long and hard over the sounds on the record, creating highly textured, richly detailed sonic tapestries that defy easy labelling. While the singer still croons like a man who could charm the pants off the Abel Tesfaye fan club, he’s added some new weapons to his game. The album’s most gorgeous track, “Pour Cyril”, starts out as an exercise in the power of classical arranging, then suddenly pulls a hard right into Arizona-badlands country noir. The breezy “Repeat Pleasure” is suaver than Bryan Ferry circa the early ’80s, while “Face Again” is marked by nightmare-inducing synth violence and wraithlike vocal fuckery.

It was only when the record was completed, Krell suggests, that he realized what he’d done from an aural standpoint. As much as “What Is This Heart?” isn’t as autobiographical as it seems, there’s no denying that Krell has taken How to Dress Well in a direction that promises exciting things for the future. That shedding of the R & B label is something he’s happy to address. Sort of.

“It’s something that you see afterwards,” Krell argues. “You’ll sit down and go, ‘Oh, shit—all of these songs are hanging together in this way, and seem to be working with these kind of lyrics and these kind of elements.’ It’s like, ‘This is crazy, and I couldn’t have anticipated that.’ And that’s kind of the vibe for me, kind of looking back and going, ‘Oh, wow. That’s what was on my mind.’ ”

How to Dress Well plays Fortune Sound Club on Tuesday (August 26).

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