Aspen's Obsession with the Trucker Hat, Explained

By Etta Meyer | July 5, 2018 | Style & Beauty

They’re seen bopping up Smuggler Trail, stand-up paddleboarding down Stillwater, dancing on chairs at Cloud Nine and drinking margaritas at charity galas. That’s right, we’re talking about trucker hats, baseball caps with a tall foam front, emblazoned with sparkly, catchy phrases across the face. For a town with serious fashion cred, Aspen seems an unlikely place to elevate such a humble accessory, yet there they are, bold and charming in their near-ubiquity.

aspen-trucker-hat.jpg"Pow," courtesy of Kristin Holbrook, @twoskirtstelluride

The hats were originally created as promotional swag for companies like John Deere and handed out in rural parts of the country; they were functional, inexpensive to manufacture and catchy. In the early 2000s, the netback, one-size-fits-all caps were appropriated by celebrities and urban youth. The ironic headwear fad burned bright and burned out.

Enter Mickey Eskimo, an Austrian former pro-surfer and artist living in Maui. As a tribute to his adopted home culture, he started hand printing Hawaiian words onto trucker-style hats. Three thousand varieties later, his brand, eskyflavor, is the cool-kid hat in surf communities from Venice Beach to Biarritz.

These are not the hipster truckers of Urban Outfitters’ heyday. “They’re like pop arts,” explains Eskimo, like having a mini-Banksy on your forehead. “It’s a dialogue. You always feel free and invited to talk to someone who has [an eskyflavor] hat.”

"Dreamy," photo by Anne Stavely, courtesy of Cyrpus Hayunga, @thehayunga

They are wickedly clever and, it turns out, thoroughly Aspen. Lee Keating and Tom Bowers of Performance Ski knew Eskimo and started selling eskyflavor hats out of their Aspen shop. Similar styles have followed en masse.

“It’s quite a phenomenon, though, right?” exclaims Tommy Tollesson, manager of Cloud Nine Alpine Bistro, Aspen’s wildest daily party on Aspen Highlands. Tollesson, along with most of his staff, wears a similar version trucker hat with “C9” on the front every day. “It started Presidents [Day] weekend five years ago,” he recalls. “It was supersunny and warm, someone came in and had one and looked cool, and it just mushroomed from there. Now it’s the first thing people ask when they come in... ‘Do you guys sell the hats?’” (Answer: They do, but storage at the mountain-top restaurant is limited and they often run out.)

"Birkin," photo by Michele Cardamone, courtesy of @leticiaherrera0212

The hats seem here to stay. Tollesson reports, “Last week I saw a hat that said ‘VAIL’ on it, and I was like, what? You can’t steal our hat.”


Photography by: