You want to look like a civilian
talking style with pro skateboarder and endurance athlete Ryan Lay
Hello, fine readers of TOGS.
North here, typing with fingers connected to arms coming out from a vest. Which reminds me: did you catch the Mudroom on vests we sent out earlier this week? If not, may I offer you this?
Today, we have a special interview with pro skateboarder and endurance athlete Ryan Lay. Ryan has been a sponsored skater for more than twenty years, riding for a string of legendary (and sometimes infamous) brands, including Nike SB, iPath, Enjoi, Welcome, Etnies, Sci-Fi Fantasy, and New Balance.
During the pandemic, Ryan got into endurance sports: first thru-hiking, then trail running, then bike packing, and not in a casual way. He started off with the Arizona Trail, and after that his first trail run took him Rim to Rim to Rim on the Grand Canyon. Last year, Ryan rode his bike down the Pacific Coast, Vancouver to Tijuana. Big outings, all of them, and enough to land him a spot on the Mountain Hardwear team.
Ryan also happens to have sick style, both on the board and off—which means we’re more than stoked to pick his brain here on TOGS today
Below, we cover why skaters dress like civilians, how Ryan got into trail running and fastpacking, why outdoor brands are doing skate aesthetics better than skate brands are, the best shape for shorts, and more.
Incoming!
North: When I think about technical clothing and skateboarding, one thing that stands out is that skateboarding seems to be the most intense sport that people do in their street clothes. What’s up with that?
Ryan: I was just talking about this yesterday. I was skating in thick Anchor Blue denim jeans and then switched to shorts because it was hot out and I was like: this is the only sport that people don’t wear athletic clothes for.
North: I remember seeing skaters do the same thing with their tiny beanies like ten years ago. It’d be 100 degrees out and they’d keep them on their heads. Why’s that?
Ryan: If I had to guess, it’s probably because skateboarding is a thing that happens in the street, and you want to look as much like a civilian as possible.
I mean, it’s actually one of the very few sports that doesn’t have any sort of technical gear. Aside from the footwear, you don’t really need any equipment. People just want to look like they would walking around in a city, but on a skateboard.
North: Civilian style—I like it. How would you describe your personal style when you’re skateboarding. Do you just wear your usual clothes?
Ryan: I remember something Jerry [Hsu] said one time when we were talking about pants. He’s like, with skate clothing, you want it to be baggy to the point where you feel a little uncomfortable going into the grocery store. The movement and the wind and the sweat slims things down a bit, so it looks better on video if everything is a little oversized.
“With skate clothing, you want it to be baggy to the point where you feel a little uncomfortable going into the grocery store.”
Lately, I’ve been really into wearing basketball shorts with a hoodie or a baggy long sleeve. You know, kind of how a boxer looks when they’re running up the stairs in a movie. That’s the kind of style I’ve been into recently.
North: Basketball shorts, huh?
Ryan: I got some of those old-school, kind of wide, 3-5”shorts when I started running, and those looked closer to what I wanted to be skating in regularly. Now, when I’m not skating in a wide pant or short, I find it to be pretty uncomfortable.
North: Totally. So many men’s shorts are tube-shaped and too skinny, which is such a bummer. I’m after something wide and flouncy.
Ryan: Yeah, 100%. That’s exactly what I’m looking for. At one point, Sci-Fi Fantasy made some that I really liked, but they don’t make them anymore. I filmed a ton of clips in those shorts. They were my favorite for a long time.
North: One thing that I associate with skate style is that it doesn’t seem to care what non-skaters think about it, whereas other sports are always looking over their shoulder, trying to figure out whether they’re cool or not. Is that perception right?
Ryan: Yeah, I think that skating is just a pretty protective culture and you end up with a lot of people who have strong opinions about things and want to set themselves apart. People often get into this argument about whether fashion follows skating or skating follows fashion, but I think that a lot of skaters want to reject whatever is the dominant norm.
In the last 10 years, we’ve seen the return of huge pants and Polar Big Boys, and now you’re starting to see a lot of people move towards skinny jeans, or boot cut jeans, or whatever they think is the antithesis to baggy jeans.

North: It almost feels as if skateboarding is constantly trying to outrun the mainstream. Like, the minute it begins to catch up, it’s time to abandon ship.
Ryan: I think the other thing is that, in this era of being hyper online, people are pulling from all sorts of different influences. It’s not like a linear trajectory where we’re revisiting the ‘90s or the 2000s. People are pulling from all over the place now, and sometimes even from contradictory places.
North: Thinking about influences, are there any cultures or sports that you see skating pulling from now?
Ryan: I mean, all the skaters are into fucking golf now, which seems bad to me. But yeah, theres’s some hierarchy of sports that are cool to pull from. No one’s trying to pull from football, but people love to pull from tennis and soccer, and now golf, too, which is maybe due to the fact that everyone’s 40 and skating now.
North: Meanwhile, you’re in your thirties, but instead of getting into golf, you’ve gotten into fast-packing, ultra running, and bikepacking. What drew you to those endurance sports?
Ryan: I think at a very basic level, it’s about exploration, and there’s a different but similar relationship with suffering. Not to be overly epic about it, but they share this quality of pushing through. That’s something that drew me to skating and definitely pulled me into endurance sports.
North: As you got into outdoor sports and started buying gear, how did you decide what to wear?
Ryan: When I started, I just was watching YouTubers, and then I met Springbean, who’s a professional runner, and then a couple other guys. They were all into Pa’lante and the ultralight world, and they got me into that, too.
I don’t have a super built upper body, and the aesthetics of ultralight backpacking were cool to me. You know: pare down your weight and pare down your life. Make everything feel real minimal. I really like that.
North: Coming from skateboarding, did you have any adverse reactions to hiking style?
Ryan: I actually like the style of all of the cottage brands—I bought an Enlightened Equipment jacket—but I do think gaiters look terrible. I also wore Altras when I started thru-hiking and I’m not terribly crazy about how those look.
North: When it comes to skate brands, skaters are known for their strong loyalties. What are some of the outdoor brands that you’re especially excited about?
Ryan: I’m really excited about Mountain Hardwear, and not just because I work with them. They’re kind of a dream brand for me. I used to search their vintage stuff on eBay, and I feel like they’re doing a really good job of getting back to that state.
In addition to that, I like Pa’lante, and my friend Danny has a bike brand called GRIN27 out of LA that does sick bike gear. I’m also kind of a diehard Gramicci fan, especially the pants and shorts. I think they’ve done a really good job of keeping their brand cool for a long time.
North: Do you have a favorite Gramicci pant?
Ryan: Probably the Gadget Pant. Yeah, those are sick.
North: I love the giant pockets on those. You can fit a paperback in ‘em.
Ryan: I have done that many times, actually.
Peter Sutherland, a photographer I did a Satisfy shoot with, also has a new clothing brand called Surroundings. I wouldn’t put it the outdoor category, but it definitely pulls from outdoor influences, and his stuff is always my favorite. He makes one-off pieces and then some screen-printed shirts. As a friend, I’ve been fortunate that he’s given me a couple pieces that I really cherish.
North: I was actually gonna ask you about some of your shirts. You seem to have a bunch of really cool, seemingly small-batch or one-off printed shirts.
Ryan: I like to wear old vintage shirts and have always really liked the feel of old cotton. I don’t really love the kind of plastic-y feel of technical shirts. They can get really clingy.
There’s a term in skateboarding that people call “gear claw.” Gear claw is when you wear the bad sponsored t-shirt. It’s not that your sponsor’s bad, but the shirt is. It’s, like, an ill-fitting Gilden with a huge Pig Wheels logo on it. If you go to a skate contest, all the kids have gear claw clothes, and as a skater you want to do something to distinguish your personal style, I guess.
North: Moving in the other direction, a lot of outdoor brands are really leaning into skate-inspired aesthetics, particularly in their marketing. How does that land for you?
Ryan: I think it’s cool, but it does frustrate me sometimes because I feel like they’re pulling from skating in a better way than the skate brands are! I’m like, come on, man, we gotta get it together! You guys are eating our lunch.
It’s this interesting paradox where skate media has professionalized and has almost become too nice looking. Many of the outdoor brands are pulling from further back in skate heritage and doing a really great job with it. You know, they’re using lo-fi video cameras and all those things.
North: For sure. Aside from aesthetics, are there elements of skate culture that you’d like to see come to the outdoor space?
Ryan: Skating really emphasizes style, and I think that’s really important: the way you present yourself, the projects that you choose, the music that you use, the branding, the art direction. I think all those things are really important to how you tell your story as an athlete. Running, cycling, and climbing are all catching on to that.
North: I especially love the sports where the movement is really expressive—where style isn’t static, but made in motion. It’s maybe the hardest to achieve, but definitely the coolest to see.
Ryan: Yeah, totally.
North: Ok, last question. What’re your go-to pieces of gear?
Ryan: I have a few go-tos from Mountain Hardwear, like the Summit Grid Hoody, which is similar to a Polartec fleece, and then the Ghost Whisperer down jacket and Alakazam backpack—that’s the backpacking bag I use all summer. I also have a Satisfy running belt that I wear almost on a daily basis. Plus, as I said, some vintage cotton tees.
My go-to hat right now is an old Tacoma Rainiers cap. My friend Alex bought it for me. I don’t really love technical hats. They’re unnecessary. You can just wear a normal hat.

A normal hat will suffice, indeed.
Ryan has some big plans ahead for the summer, including a bikepacking trip that’ll take him from the northernmost city in Alaska all the way down to Seattle. He sets off in June. You can follow along via his Instagram.
Bon voyage, Ryan, and thanks for joining us here at TOGS.
- North 🤸
Off the Grid
Organic shapes, wrinkly textures, dangling adornments, and layers of brown and yellow 🌻










