Menswear nerds, assemble: This week’s subject is comedian, actor, writer, producer, travel show host and fellow jawnz enthusiast Adam Pally. After exchanging some DMs about a particularly spicy outfit of Adam’s, I suggested we bring his sense of style to Esquire’s readership. Pally’s new travel show with comedian and close friend Jon Gabrus, 101 Places to Party Before You Die, is out now on HBO Max; it’s hilarious and easy to watch. Pally is also starring in a new comedy called Who Invited Charlie? and he’s been performing with a guitar at various comedy clubs throughout New York City, where he resides. So, yeah, there’s a lot happening.
Adam and I sat down a few weeks before the premiere of his new film to talk about partying in Miami, Kanye West and Eddie Vedder, how comedy relates to fashion, and plenty more.
Do you remember your first big break?
I don’t know if I’ve ever had a big break. It feels like I’m still clawing and scratching to stay around. I remember I was very lucky when I first started out at Upright Citizens Brigade because it was small. Comedy—improv and sketch comedy, especially in New York—was not a big group. It was mostly coming from Chicago and a little from L.A. So those of us that were there early, we were kind of fast tracked to become New York commercial actors. I wouldn’t call it a break, but I remember I did a commercial for Staples with a cat, and it was the worst day of shooting ever. It was my first day of real work. And you’re working with an animal and you’re like, “Ugh, if I only knew how much I would be working with animals for the rest of my life.” The commercial premiered on NFL Sunday. And I remember people calling me or my parents, so I guess commercials were my first whiff of “something’s happening.”
You currently star in a show with Jon Gabrus called 101 Places to Party Before You Die. What’s your history with Jon, and how’d the show come about?
I met Jon at the UCB. We got put on the same comedy team together and we just hit it off instantly and then started touring a lot together. When we would tour, we would notice that we had similar interests in traveling, which was mostly just to get fucked up and eat food and see shit, which I guess is pretty much just being alive. But sometimes when you’re traveling, the other people you’re with, they’re not on your same vibe. We felt that way young with no money, so once we got a little older, we thought, “I think that there’s something funny here,” because we’d just consistently do bits. “Let’s do a travel show that’s less about the travel and more about the bits.” And that’s what it was.
I just watched the Miami episode yesterday. And you were wearing a suit on a boat at one point, and you have a tucked denim shirt in another scene. Do you have any style advice for people that are traveling to a different climate? It looks like you don’t give a fuck about what the temperature’s going to be.
I don’t. Kanye—may he rest in peace, in this household—he had a quote once that was like … I’m not going to do the quote justice. It was something like, “Yeah, I look fly no matter the temperature.” I kind of live by that too. You need a summer beanie, especially if you got cabbage like me. The climate in Miami will screw up your ‘fro to the worst. I feel like in Miami, you need a lightweight suit. They don’t let you in if you don’t have a lightweight suit.
Your man says a Speedo; you’re in a full suit.
Well, to Jon, a Speedo is formalwear. We had to talk him out of wearing a Speedo to the Emmys.
How do fashion and style factor into your life?
I like repetition. If you find your lane, you find the things that fit in your pattern. At an early age, I found what I liked. From then on, it’s an endless search to level those things up into nicer versions, or newer versions, or sometimes older versions.
What first piqued your interests?
My wife owned a clothing store when we first got married. Most of my clothing is old, vintage. I always like that because I’m built like a 1920s boxer, so I need clothing tailored for Cinderella Man. No legs, giant torso, enormous head, tiny alligator arms, chubby hands. I’m built like a cartoon drawing. I would search eBay at a young age for vintage, and I knew what I liked. But then when I saw the business up close and I saw how she bought, how her eye and her style were reflected in the thing, I became interested in it. “How does a brand work? How does a brand work with a client?” So, I guess now I’m interested in the business side of it, too.
Do you have any style inspirations or people whose style you admire?
I always love Kanye.
May he rest in peace or power? Probably better for me if it was peace. I think it would be disingenuous to all of a sudden now, because of the last year, not mention him. I still think he looks cool even now, old and dusty. I still think he’s thinking a step ahead. Besides him, I think most of the style inspiration I take is from contemporaries or friends of mine. I think Larry [Schlossman] is the coolest. He’s the source at the moment, just in vibe. I don’t see him brick ever. I like his shit. Aaron Levine. Aaron’s a guy that I like; it’s like Americana in a way. He looks like the best version of an Eastbay catalog.
So basically, two fashionable Jews and one person that hates them. It’s embarrassing, but I send my friends pictures of Eddie Vedder sometimes. I think Eddie Vedder is the coolest dude. I don’t know why. I always thought he was so cool.
Sometimes it’s deeper than the gear you put on, too, that informs what you’re wearing. You can wear just a regular flannel, but if you’re fucking cool, that makes that regular flannel…
A little cooler. I just feel like Eddie … He would do shit when I was a kid that I still mimic today, like a backwards fitted hat. That’s from the “Jeremy” video. It’s been taken by baseball players, but that really was like Ken Griffey Jr. used to do it at batting practice. Eddie Vedder lived in Seattle, and then he started doing it. And then it was in the “Jeremy” video. And then you had 13-year-old me with my hair parted down the middle and blown out by my mom stuffing it in a backward Chicago Cubs fitted hat. Vintage Robin Williams. I looked at those pictures so much. I feel like I’m in my Robin Williams Issey Miyake phase.
Talk to me about some of your current favorite brands and stores.
I still love John Elliot. You haven’t had this yet because you’re 30. But as you approach middle-age, men go through something called a thickening, and I’ve gone through my thickening, and it’s very hard to remain stylish in your thickening. And John Elliot, his sizing is very good for me. And I like his elevated stuff, like his leather. I wear a lot of Ralph Lauren and a lot of old Ralph, like vintage Ralph Lauren. I like that Americana, luxurious hippie vibe, elevated lumber-Jew J. Crew. I think they had a good year. I really liked it.
I shop a lot of vintage stores mostly. Digitally. I feel like a lot of my stuff comes from packages that are wrapped in plastic bags and you’re pulling them apart and dust is flying everywhere. And then you have your great pair of vintage Levi’s from the Philippines. I’d have to go through my Depop…
You’ll gatekeep those?
No, I don’t want to gatekeep.
2023 is a year of no gatekeeping. But don’t tell anyone where I live.
What is comedy to you?
Comedy is surprise. Jordan Peele’s talked about it. I don’t want to speak for him. The reason horror and comedy are so close is because it’s surprise, right? To get a laugh from you, I would say or do something that you weren’t expecting, or you were, but I fulfilled the expectation in a way that brought you joy, so you would laugh. In the same way, if I were to scare you, it would be because I would surprise you or fulfill an expectation in a way that you didn’t think would happen and you would be scared. It’s the same kind of button that you’re pushing. To stay relevant and funny, I think you have to consistently be pulling back and thinking, “How does this look in the world? How does this fit now, contextually, not just in my career, but in the world?”
Do you think comedy and fashion have any commonalities?
I think similarly, fashion is the ultimate mirror of people looking at the world, being like, “What’s in? What are people doing? What’s collectively becoming a thing?” And then, “How am I using that and fulfilling the expectation or subverting the expectation?” Trend is similar, I feel, to comedy in that way, where it’s like, camp-collar shirts have a moment where they’re really cool for a couple years and you could buy any camp-collar shirt, but the one that you pick is going to reflect how you feel in that moment the same way that the joke that you tell is reflecting how you’re telling that joke.
If you had to pick one outfit to wear for the rest of your life, what would that be?
You want that mix of comfort and style, like you could walk in anywhere because if you’re wearing it for the rest of your life, you want it to be super versatile. I think I would look like I got an internship at Tom Sachs’ artist studio. It would be raw denim, plain Nikes, a white button-down shirt and a blue chore coat. Because I feel like I could still get into a nice restaurant in that, but at the same time I could sleep in it.
Christopher Fenimore is a writer and photographer living in New York. Working with clients ranging from clothiers to vineyards, he’s also covered street style for a number of outlets. Follow him on Instagram at @c.fenimore.