Role Model Wears Jeans to Bed (He Showed Us)
One scroll through @rolemodeloutfits, and you instantly realize that Role Model is always wearing jeans. If he’s not wearing jeans, then he’s wearing a denim jacket. In many cases, he’s wearing both.
Hardly any fit is unnoticed by the fan-run Instagram page, which tracks the daily outfits worn by the musician, born Tucker Pillsbury. A true Outfit Repeater, Pillsbury’s favorite type of clothing is some form of vintage denim, often paired with a graphic tee. Chuck on Tour, his biggest global headlining run of his career, is no exception to the rule.
He may as well trust his Evisu Daicock jeans with his life, even as his collection of secondhand Levi’s silhouettes grows and straight-from-Hawaii Sugarcane denim speaks to him more than any venue he’s performed at. “I get sentimental about clothes,” Pillsbury tells me over Zoom on a rare off-day after his Radio City run of shows. Chuck on Tour brings the musician's 2026 studio album, Chuck Timely & the Hourglass to life through a career-spanning setlist, a palpable stage presence, and, of course, an array of denim — a lot of which he actually sources on the road in between shows.
Currently at the midway point of Chuck on Tour, Pillsbury doesn’t know where he’s heading for his next show; he doesn’t “like to think too far ahead [because it] stresses me out.” He approaches fashion the same way. Packing for tour isn’t what’s most important, but rather, it’s scouting vintage stores on Instagram to shop at along the way. Before he heads out to one he’s been eyeing in Buffalo, Pillsbury explains what exactly defines Role Model-approved denim.
Where am I catching you on your day off today?
It’s a rare day-off in Buffalo today. There’s a vintage spot I found that I’m really excited to go to.
Is that something you make sure to do in new cities?
I shop a lot. I mark every vintage store I want to go to in every state. This tour, I'm hoping to shop at every stop.
How do you find these vintage spots?
My new technique is just opening up Instagram and typing in “vintage stores.” Like, I forget, you can just kind of just search for stuff like that. I look at the selection, and I lean towards things that are a bit curated.
What do you pack with you for tour?
I didn't pack until the day before. I was not thinking about tour at all. I pack what I think I need, and then I do lots of shopping.
Which city are you most excited to visit on this tour?
I’m most excited to go to Atlanta for the shopping. There’s amazing vintage there.
Are you aware you have a really devoted outfit Instagram page? It’s updated literally every time you step out…
I'm very impressed by the @rolemodeloutfits account. The amount of things they get right is really fascinating. I don't know how they do it. I will say, a lot of the time, they get the jeans wrong, though. I'm in, like, a month-long period where I'm just wearing the same outfit every day. I don’t get sentimental about venues, but I do get sentimental about clothing, so if I get a new shirt that I love, I'm gonna wear the fuck out of it for a month. You get roasted on the internet. But I don't care. I’ll never change.
What are some pieces in your closet you have a strong sentimental connection to?
All my jeans. I’ll never have enough. I don't want to say the place, but there's a spot in LA that I go to that has the most amazing selection of vintage Evisu. They also have a bunch of rare Levi's, which I’ve always loved, and cool Sugarcane denim from Hawaii. It's that stuff that I connect most with, but I have a lot of fun vintage stuff. I have some vintage Bean bags that I'm sure are worth a lot of money in Brooklyn or something.
Are you a big Japanese denim guy?
I don't know anything about it, really. I'm learning about it, as is everyone right now.
What makes a good pair of jeans?
It’s all about the fit. I'm obsessed with how things fit. I like being comfortable and I like wearing things, especially jeans, that fit me.
What about a good T-shirt?
It’s the same thing with shirts. I don't give a fuck what a T- shirt says. The one I’m wearing says “Mount St. Helens, Washington.” I couldn't even point to it on a map, but it fits perfectly. The back says “She’s about to come,” and I was that connected with the album rollout when I bought it. I like to find things that feel like they're an extension of me. I just buy whatever speaks to me.
How do your personal style and your music inform one another?
They’re both a little messy, probably, and a little sloppy and rough around the edges. Nothing's perfect about the music and nothing's clean cut or perfect about the way I dress, but everything is cohesive.
Are you thinking about how things are going to look or translate on stage, or are you more so picking up pieces you personally like and want to wear?
I discovered tailoring about two years ago, and that makes shopping more fun because I’ll just buy anything I like and just tailor it. Every T-shirt I can hem a little bit or bring in the sleeves however I want. I get a lot of cool flannels and button downs and have them tailored to fit just right. The line between what I wear on stage and what I wear on an off day is almost nonexistent. It's the same.
So are you wearing jeans at home? On a plane?
I wear them in bed.
In bed is crazy…
Jeans are my sweatpants.
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