The mindset behind Malcolm Todd‘s wardrobe can be summed up in one simple sentiment: if everything in his closet is cute, every outfit will ultimately be okay.

“I could dress myself with my eyes closed if everything’s cute,” Todd, the starring musician in Gap‘s new GapDenim campaign, tells Hypebeast.

That guiding ethos has informed a myriad of distinct Malcolm Todd™ looks: a “Roommates” music video outfit in which colorful barrettes contrast with a grey wife beater,  a shirtless The Tonight Show with Jimmy Fallon debut in just boxer shorts, dark denim jeans, and flip-flops, and an Instagram feed (and burner account) full of fit checks.

“I’ll wear dress pants and sandals. I’ll go to the bar in sandals,” says Todd when asked for a fashion hot take. “I just like to let my toes breathe. Dogs out. There’s nothing wrong with that.” He’s also a firm believer in the power of “a little funny accessory” in shaping an outfit. “A necklace or some funny glasses goes a really long way,” he adds. “Being a little bit random is refreshing.” Todd’s willingness to experiment melds with his affinity for classic silhouettes — loose button-down shirts, thick-framed eyewear, and, of course, really good denim — to shape his unique personal style.

Having found comfort in his own effortless, Americana-esque-but-with-a-slight-edge personal style aesthetic, it makes perfect sense that Todd, alongside Obsession‘s Inde Navarrette, finds himself fronting Gap’s “Denim on your own” music video.

The musician was tasked with reworking Robyn‘s classic dancefloor cut, “Dancing On My Own,” which Todd found to be a healthy exercise in creativity. “To me, making music is all about being fearless,” explains Todd, that exact fearlessness allowing him to step into the role of a model and dancer with utmost swagger. “This felt a little less natural at first, but everyone on set helped me feel comfortable in trying things that I’d never done before.”

Ahead of his largest headlining tour yet, the musician sat down with Hypebeast to chat all things personal style and “Denim on your own.”

How would you describe your personal style, and how does it tie into your music and creative output?

Malcolm Todd: The biggest correlation between my style and my music is authenticity. I feel enabled to wear whatever I feel, and I feel enabled to write whatever I feel. I’m very lucky to have that confidence in myself, and I think that comfort allows me to try new things and grow and evolve.

If you had to sum up your approach to styling yourself, how would you do so?

I shop with the mindset of: if everything’s cute in my closet, it’ll be okay. I could dress myself with my eyes closed if everything’s cute.

Do you have any fashion hot takes?

For sure. To start, not too much of a hot take, but I definitely like to wear a sandal with pants. I’ll wear dress pants and sandals. I’ll go to the bar in sandals. I just like to let my toes breathe. Dogs out. There’s nothing wrong with that. To me, a little funny accessory, like a necklace or some funny glasses, goes a really long way. I like wearing big shorts and a business casual top. Being a little bit random is refreshing.

You love a good pair of jeans, so it only makes sense you’re fronting this Gap “Denim on your own” campaign. What defines good denim to you?

The wash that connects to your soul and the fit that connects to your legs. [laughs] That’s about it.

As you gear up for your biggest tour yet starting in September, how do you work to curate your wardrobe for the road?

[laughs] I’m a last-minute packer. For anything pre-show and post-show, I will literally just point at things like, “That’s cute,” and throw it in the suitcase. Then I open it up and pick each outfit the day of. I don’t calculate that stuff too much. For the shows, I work with one or two of my buddies who are stylists, and they’re just constantly pulling a bunch of cool stuff to help me put together outfits that I feel comfortable and fly in.

Did working on “Denim on your own” leave you with any creative takeaways you’ll take with you on the road?

It’s always like an exercise to do something out of your exact wheelhouse. This Robyn song isn’t exactly a song I would make, you would think, but exercising my brain and understanding the song for what it is and how I connect to it opens up my mind as a creative and a musician.

“I shop with the mindset of: if everything’s cute in my closet, it’ll be okay. I could dress myself with my eyes closed if everything’s cute.”

Also, the performance aspect of the campaign and being able to get out in front of a big set full of people and own that moment was cool for me. It instilled some confidence in me to go out and perform in front of these big crowds.

Zooming in on the song itself: “Dancing On My Own” is obviously such an iconic song. Where do you even start when tasked with covering such a legendary track?

The creative process starts with being able to walk into it fearlessly. To me, making music is all about being fearless. If you’re afraid, you’re not going to be able to reach your full potential as an artist. Gap instilled that fearless energy in me. They didn’t tell me to, you know, “Make a copy of the song,” or have me follow any specific rules. They just told me to use my voice and really made me feel like my individuality was the superpower in all this. So I really just went in there excited to see how I could use my voice to make the song special.

“I feel enabled to wear whatever I feel, and I feel enabled to write whatever I feel.”

Could you elaborate on your connection with Gap and what it means to you to lead this campaign?

The main word is “iconic.” Or “timeless.” Gap has been ingrained in my mind for as long as I can remember. It’s always been something very classic and something that everyone can wear. I remember back-to-school shopping at Gap with my mom, being at the mall and seeing a huge Gap poster with just like the three letters. All of it is just ingrained in our culture, so it’s such an honor to be a part of it. On the music front, too, Gap has partnered with so many artists. It’s a huge honor. I feel like a part of history.

The visual really feels like it belongs in the Malcolm Todd creative world. I know you brought on videographer Tanu Muiño, who you often work with, along with additional direction from Calvin Leung, Alastair McKimm, and Bjorn Loos. What was the collaboration process like?

Even though it was big, the set was very fun. I got to bring in all the people who I work on my own music with, which was really special. It was basically just another day at the office, cracking jokes, trying things out. Just like in the studio, on set, I felt I could very much be myself around everyone, and Tanu definitely helped set that tone. She’s very fun and bubbly. The second I met her, I knew I could just try whatever creative direction I wanted with her, and that’s exactly what we did here.

I’m a musician before I’m a model, so this felt a little less natural at first, but everyone on set helped me feel comfortable in trying things that I’d never done before. I’m not a professional dancer, but they made me feel like one in a way. It was a really fun process, and I learned a lot during it. I have the best job in the world.