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Do the Trail a Favor: Wear a Weirder Hat

When hiking becomes cool, it loses something sacred.

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People talk all the time about the benefits of hiking. It’s good for your heart! It’ll reduce your stress! You’ll lower your cholesterol! Blah, blah, blah. Those people have it all wrong. 

Sure, walking up hills will give you buff calves and sexy toe calluses, but the biggest, most overlooked benefit of hiking is that it gives you the opportunity to get real experimental with fashion. I’m not just talking about dabbling in zip-off pants and fugly sun hats (though if bucket hats can make a comeback, anything could happen.) I’m talking about the nearly untapped potential for self-expression—and the secret to unlocking the heart and soul of hiking itself.  

But before I can explain what this means to me, you have to understand where I came from. 

I spent my childhood being one of the least cool kids at a series of fancy prep schools in north Atlanta. There, it felt like appearance was everything. I knew of classmates who got parent-sponsored plastic surgery, and others who wore $150 haircuts with highlights. I remember spending weeks planning my outfits for “dress-down days,” the rare breaks we got from our uniform plaid skirts. I’d carefully analyze which department-store jeans were cooler and agonize over whether to wear stud earrings or risk the hoops, which were just bigger than a dime and therefore flirting with the limits of the dress code. (What can I say, I was a rebel.) 

All I wanted was to fit in. As a member of both the mathletes and the school theater troupe, I never really stood a chance. I tried to develop a sense of style. I developed an eating disorder instead. 

Then, I went away to college. A few semesters in, I fell in with a group of hikers and backpackers that called themselves The Tramping Club. At one of the first club meetings I attended, I met one of the founders. I was shocked: She had unshaven legs. She had a nose ring and dirty sandals, wore some kind of artistic interpretation of tie-dye, and she looked like she hadn’t washed her hair in weeks. And she was the coolest one there.  

Intrigued by these strange, hairy hippie people, I signed up for my first backpacking trip. I borrowed a pack, hopped in a minivan, and was ferried off for a weekend trip in Virginia’s Grayson Highlands State Park. 

At that point, I think the three-day trip was the longest I’d gone without looking in a mirror. It was also the first social setting I could remember where no one mentioned their weight, acne, or anything about their outfit. Clothes were suddenly just about functionality. The only good hairstyle was the kind that would keep your hair from sticking to your face. Scabby shins were a point of pride. 

At first, I was lulled into thinking that hiking fashion meant no fashion. Then I started meeting thru-hikers. That’s when I realized that there is such a thing as hiking fashion, and that it is an art form, maybe even high art. After all, these were people who were so liberated from the vagaries of trying to fit in that they were veering fearlessly in the opposite direction. What is that if not art? 

Here’s what I came to understand: When it comes to hiking fashion, the ultimate goal is to look like you got dressed in the dark with your eyes closed. And if you actually did get dressed in the dark with your eyes closed? All the better. I met a guy thru-hiking the whole AT in a pair of homemade pajama pants. Another wore an entirely nonfunctional straw hat full of holes. There were colorful Dirty Girl gaiters, mismatched socks, and quantities of paisley and plaid that defied logic. There was everything you can imagine, and worse, and more. 

I’m talking hiking kilts and socks with sandals. I’m talking Karate-Kid bandanas and upcycled middle school soccer jerseys. I’m talking garments pulled out of rivers and items liberated from lost and found bins. I’m talking clothes that not only look awful, but smell awful, too. That, my friends, is a multi-sensory fashion experience that few dare to reach for. 

“At first, I was lulled into thinking that hiking fashion meant no fashion. Then I started meeting thru-hikers. That’s when I realized that there is such a thing as hiking fashion, and that it is an art form.”

I spent the rest of college going on backpacking trips every chance I got, happily wearing the same shirt, bandana, and mismatched socks on every one. My roommate told me she’d never smelled someone from so far away before. I’d never felt freer. 

When I graduated, I moved out to Colorado, where I’d heard there were bigger mountains and even better trail access. What I didn’t expect was to find myself back in the Land of Beautiful People—the land I thought I’d escaped. 

Out West, I discovered, hiking wasn’t a niche hobby that weird hippie people did on weekends. It was a competitive sport. People had hiking outfits. People dressed to look cute on the trail. 

For a while, I fell into this, too. I bought more stylish climbing pants, in brighter colors just in case someone happened to take my photo and tag me on the internet. I hid away my old hand-me-down college backpacking shirt. I wore clothes that I thought would make me look more like a Serious Athlete instead. 

Then, a few years back, I went on a hiking trip in California with a few of my college friends. 

“John,” I texted from the airport. “I forgot a sun hat. Do you think you can lend me one?” 

“Sure,” he said. When I got to his apartment, he handed me a hat. It had legs. 

It was more or less a ball cap but it was bright red and styled like a giant crab complete with googly eyes and plushie claws that hung down over the wearer’s face. At first I rolled my eyes in disgust. Ugh, I thought as John giggled. Why can’t he grow up? 

But then it dawned on me. It wasn’t John who had failed to grow. It was me. I was trapped in North Atlanta, in Boulder, in Instagram. I’d forgotten what it meant to be free—truly free—to be silly and goofy and outside and alive. 

There’s nothing wrong with loving style or design, or dressing in a way that makes you feel confident. But I think we lose something important when we let the outdoors—and outdoor fashion—become subject to the same rules and constraints that suffocate us at home. I think we all need someone to come in every once and a while and remind us: It’s OK to wear your legs unshaven, your hair greasy, or your socks mismatched. 

The trail doesn’t care what you look like. The trail doesn’t care how you dress. The trail doesn’t care if you have a muffin top or stained shirt or a hat full of holes. In fact, if the trail had any opinions whatsoever, I think it would prefer those things. Because when you wear something goofy, it keeps you from taking the trail too seriously. It keeps you from seeing nature as a set piece for your burgeoning internet popularity, or as a thing to be conquered. Instead, you see nature eye-to-eye, without pretension. That’s how real relationships are born. And the more real our relationship with nature is, the better off we’ll all be.

So, let this be a challenge: Next time you go hiking, don’t take any selfies. Get dressed in the dark with your eyes closed. Wear the clashing colors. Wear the hat with legs. Wear the hand-me-downs, the baggy shorts, the mismatched socks. Wear something practical, comfortable, and fun. Because that’s what walking around in your own skin should feel like. 

And that’s a feeling none of us can afford to forget.


From 2022