Maybe it’s just me, but has anyone noticed that clothing styles in Bend have gotten a little bit …hipper? And, to that end, dirtier?
I moved back to Bend from Portland in April. In the years I’ve been gone, a lot’s changed — not least of which are the varieties of styles cyclists are rocking on Bend’s ample trails and gravel roads.
I love what I see.
Instagram memesters like @Doomscroll_forever have dubbed this look “dirt bro,” but it transcends gender. Many ladies have tackled the style and turned it into something tomboyish yet decidedly feminine. And plenty fun. In place of roadies’ Lycra Superman suits or the moisture-wicking baggies preferred by mountain bikers, this cycling tribe is opting for a more rugged, dive-bar casual look while shredding on bikes.
Imagine lived-in Carhartt vests, overalls and coveralls. Black, brown and navy work shirts, sun-bleached, sometimes smeared with grease. Grimey five-panel caps. Punk band tees — sometimes cropped above the belly button — and beat-to-hell canvas Vans or thonged Tevas (yup, those ones). Tattoos are often geometric; they might depict the chemical makeup of DMT. Others are jokey — a Rainier beer can with anthropomorphic legs, for example. Haircuts are random. Asymmetrical, house party-administered bowl cuts might pair with braided rat tails. Eighties baseball coach mustaches are popular, yet not mandatory. For gals, Bettie Page bangs are both cute and practical. Outsize aviator glasses — I’m thinking Jeffrey Dahmer — round out an androgynous look. It’s equal parts bicycle messenger/hardcore commuter mixed with whiffs of indie musician Mac DeMarco’s shrimp fisherman vibe.
The Bend epicenter of this style is, arguably, the Kook Cruise, a Wednesday evening group trail ride that local riders Irish Fagan and Sebastian Ospina began in 2021. (Sadly, the leaders have paused the ride through fall and winter; it’ll pick back up in spring.) While the Kook Cruise originated as a laid-back way for friends to catch up each week while shredding trail, it’s since merged with the Trail Kooks, a twice-weekly running club with a robust social media presence, sponsors and organized events like the Butte Bash series.
Fagan, 28, and Ospina, 30, both work at The Commons Café & Taproom. They’ve kept the Kook Cruise low key. Attendees favor gravel bikes, often weighed down with racks, baskets and handmade frame bags, lending a ready-for-anything vibe. (They’re also packed with beer.) Curved, vintage handlebars are more likely to receive compliments than carbon fiber wheel sets. Others prefer hard-tail or dual suspension mountain bikes. One dude, astonishingly, rides a road bike. That’s the “run whatcha brung” attitude that regular Kook rider Susan Oh says pertains to both bike setups and clothing get-ups. Some Kook riders who are newer to cycling might wear running shorts and sneakers. Others might stick with mismatched spandex and fanny packs. All are welcome.
“There’s this non-self-consciousness that is hard to come by in a very social media-saturated world where you see what everyone else is doing,” Oh said. “I’m thinking of Irish’s commitment to riding in no-show socks. We’re like, ‘What are you doing, dude?’ His style evolves in this total bubble.”
The Kook crew caught Oh’s attention when she moved to Bend from Philadelphia via Sonoma County in 2021. Oh, who’s now 41 and works as a nurse, said she had thought that the scrappy, urban riding culture — one she shared with Philly friends who worked as bike messengers — was something firmly in her rearview mirror. Then she met the Kooks. Fagan, Ospina and others were riding 100 miles around Compass Park — in January. Fagan wore cut-off shorts; someone rocked jeans. Oh joined them for 20 miles punctuated with beer breaks.
“I love that there is this crust punk aesthetic: ripped denim, thrift-store tees, even Crocs,” Oh said. “A lot of Bend group rides are very focused on self-improvement or performance. I think that the Kook Cruise’s lack of uniform is really nice. If you go to a lot of other rides, people are dressed very similarly.”
Fagan, the ride leader, wasn’t available for an interview; he’d just completed a 1,000-mile bike tour through Germany, Switzerland and France and was still bouncing around the continent. He typically steers the group, which number between 20 and 50, through semi-improvised routes that connect bike paths, organically stomped foot trails and the plethora of single-track and gravel routes that crisscross the Deschutes National Forest. Sebastian Ospina rides in the back, making sure no one who, say, gets a flat tire, is left behind. The pace, at least at the front, is sparky; frequent regroups allow party-pacers to catch up while front riders crack beers and pass them around.
Kiersten Rowles, an avid cyclist who’s a regular at the Wednesday evening Kook Cruise, says, “these are my people.” A hairstylist by day, Rowles is also a daily bike commuter, riding in all weather to her stylist gig at Badlands Hair Studio. Rowles joined up with the Kook Cruise last year.
“I like the Kook Cruise’s camaraderie — nerding out about bikes and well as the way we show up in our respective styles,” Rowles said. “It’s like being a kid and dressing for the playground — it reminds me very much of the Lost Boys from the [Peter Pan] movie ‘Hook.’”
Rowles began cribbing from the urban riding steez she encountered during three recent years in Portland. Cut-off shorts, even jeans — without chamois padding — are de rigueur. Breezy, easily unbuttoned Hawaiian shirts are go-tos. Band tees are conversation starters. Vans sneakers and a camp cap, shoved under a helmet, finish the look.
“On the Kook Cruise, we have no attachment to an outcome,” said Rowles, noting how a recent Kook ride involved a group dip in the Deschutes River. Fagan crashed into the water, still attached to his bike. Everyone cheered. “It’s looser that way. We’re just here to have fun.”
This article appears in the Source September 25, 2025.
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