I think one of the reasons your interest in menswear seems exceptional is that it seems unconnected to your musical career—a totally different creative lifestyle.

Well, it’s only different if you look at the genre of music as the definer of what culture you can be involved in. I mean, I was sort of horizontal before anyone else went horizontal in terms of just breaking down the barriers. Because I was always far more interested in stuff other than the scope of music that I made. And so if you take the musical genre partitioning away, then none of it’s all that strange. It’s just that I don’t necessarily connect my interest in fashion to the main event of what I do musically.

The only key to access is curiosity and looking into developing a sense of taste—that goes well beyond fashion taste, right? This is the real thesis of the whole thing: fashion is now available to everybody. You don’t have to wait in line for Supreme. It might actually be easier to get it on eBay, in terms of cost-benefit. Right? That’s no longer the barrier to entry to get the shirt or to get the record or to get the skateboard deck or to get the brick. And it’s the same thing with music, it’s the same thing with filmmaking, it’s the same thing with every aspect of art. The access is now completely uniform. Anybody can make a record, anybody can have a band, anybody can make a film. Anybody can have a website, anybody can start an initiative, whatever they want to start.

“I’ve lived enough of feeling like I was almost gonna get hit by a car for four lifetimes.”

Anybody can screenprint T-shirts, come up with a brand name and be a designer.

Anybody. That’s right. But, the new metric is your level of balancing different tastes, creating your own tastes out of them. Literalism is dead. Literalism is gone. Even the literalism of Free & Easy magazine, like, going head-to-toe with it, or Supreme head-to-toe. Literalism is easy now because all you have to do is click follow on an Instagram account and it’s a subscription to a certain amount of cultural influence. So the real question—or the only question I’m interested in—is how do you implement that in a way that’s authentic. And you can even push the boundaries of authentic, right? Even authenticity is up for debate.

Do you think you’ve achieved a sense of authenticity in your life, in your interests and style?

I think so. I think it probably works by way of, like, two steps forward, one step back, repeat. I’m OK with dismantling something that works in order to find something else that works down the line.

This might be a sort of obvious comparison, but your music and style seem to have paralleled, and become more refined and rarified simultaneously.

I think you’re right. There are so many lyrics on Room for Squares it’s ridiculous. If you look at the length of people’s lyrics when they’re younger, it’s clear they just have more thoughts. They produce so many great first takes. But think about an older jazz horn player. They won’t play as many burning lead lines. There are more conservative, efficient ways to say things. When you’re 24, you want to get mainlined ideas, you just want to get mainlined pure, uncut thought.

The greatest thing about music is that you can just keep showing it—you can’t keep showing the same movie in a theater, you can’t keep doing the same standup comedy set. But I play Continuum every night. I play “Slow Dancing in a Burning Room” every night. So what I’m looking for as an artist is stuff to supplement that. Think of it like collecting. It’s really easy to collect the first 80% of anything, and then you spend the rest of your life trying to hunt down the rare shit. And what I’m trying to do now is hunt down the really rare-shit music. You know? I’m into the exploration of having your shit down. Because I’ve lived enough of feeling like I was almost gonna get hit by a car for four lifetimes.

I have to say you seem pretty fulfilled going into 40. What’re you doing right?

The reason I’m so happy now is because a lot of expectation that I had for myself was probably a little bit unnecessary. I have a perfect image of ambition and reward for my life right now. I know what to expect, I know how much I should be asking for when I knock on the door, and I get it. I really write down on a piece of paper what I want out of life and what I want out of work and what I want out of “fame”—and I have all the stuff I want. And, yeah, I would probably like another 10, 15, 20%, but that comes with another 85% of headache. [laughs] That’s the truth. It would take another 85% of my happiness to get another 15% to 20% famous and, like, culturally relevant or whatever. You know?