How to Choose a Hiking Hat That Fits Your Personality

Apologies to anyone who encountered me on the Pacific Crest Trail in July 2021, rabidly racing in circles through the wondrous Marble Valley in the northernmost reaches of California. Indeed, had you been peering down from Marble Rim, which juts from the brilliant forest like some rough-hewn countertop slab, and watched me sprint around the meadow below, you would have worried 1,600 miles of the PCT had finally driven me mad. But you see, I was just trying to get back my hiking hat—from, that is, the diabolical deer who had stolen it. Not crazy at all, right?

To backtrack: Two years earlier, just days into my hike of the Appalachian Trail, a new friend had dubbed me “Gunner,” not because of my speed or because of some military past that does not exist. Instead, I looked like an athletic Elmer Fudd, with my zip-off cargo pants, yellow-tinted sunglasses, and blaze orange Filson hat. I wasn’t hunting wabbits, but I simply thought that’s how long-distance hikers moving across such ancient mountains and hollers were supposed to dress. Gunner became and remains my trail name, a badge of honor in spite of its embarrassing origins.

By the time I began the PCT, I understood trail fashion was much more flexible—tiny running shorts from France, toe socks in all colors, a lightweight sun shirt in whatever shade I fancied. I also spent an absurd amount of time considering the perfect hat, which I saw as the bumper sticker of hiking couture, a way to say a lot about your personality and interests with a single pithy statement. So when I came across Gunner, a Nashville-based manufacturer kennel manufacturer for folks who hunt alongside dogs, I knew I’d found my match. My forest-green Gunner hat, with waterfowl taking flight behind the name, was not only a nametag but a little joke. I knew very little about guns or hunting, but here I was, a Gunner walking through the woods.

And now, this deer—loitering near a PCT shelter in the Klamath National Forest, waiting for us worn-out hikers to drop crumbs of the precious calories we carried—had lifted it from a log, chewing on its sweat-stained rim for every bit of salty magic it could stand. I chased it around the woods for 15 minutes, at least long enough for the rest of my trail family to arrive, point, and laugh, less at the deer than my bad luck. It eventually disappeared with my hat clutched in its jaws, a victory swiped from the head of humanity. For the final 1,000 miles, I carried on in a series of hats I never really liked, occasionally grumbling about the Klamath deer that had replaced me as Gunner along the PCT.

These days, I take my pre-trail hat selection perhaps a little too seriously, considering not only how it feels on my head but also what I want it to say about me. You’ll likely find me in a blaze orange baseball cap—available at most any hardware store in any town in the United States for about $5—hand-stitched with some memento of a state I’ve already crossed. For the last few years, I’ve often sported a patch from Cypress Gardens, Florida, found in a Santa Fe thrift store, atop my hat; it’s an invitation to talk about the most fun National Scenic Trail, the Florida Trail. My alternate, another orange beauty from a California horse-and-hiking outpost called Kennedy Meadows Resort, is a kind of nod to other PCT alums, a chance to rhapsodize about the Rotho-like beauty of nearby Sonora Pass.

You can express yourself in so many silent ways on trail, from your backpack brand to the food you eat. Everything you carry is often a direct reflection of a value. But there’s no simpler, cheaper, and more functional way to do this than with a good baseball cap with, perhaps, a few well-chosen accessories. Sure, there are other hats—the bucket hat, the sun hat, even the humble visor. I don’t think these comparatively lame pieces of headgear work better or say something that flattering about you. Here’s why the ballcap still rules.

You Can Wear a Sun Hat or a Bucket Hat, but…

I turn 41 in a week. I am a fair-skinned dude with thinning hair, and I’ve spent at least half of those years either going too hard at rock shows until late in the night or trekking for hours on end in the sun, rain, or snow. I don’t need any help looking older. But that is exactly what you get with a sun hat or a bucket hat, pieces of anti-anti-aging technology so powerful I hear they are in with the kids again. Still, their appeal outdoors seems intuitive, right? A wider rim that encircles one’s head provides more shade on all sides. But have you ever worn a sopping wet bucket hat? How did that feel? And have you ever worn a wet bucket hat in rain that lasts three days or tried to strap that soggy mass to your backpack? Good luck with that. Both of these styles also serve as sails, so prone to being lifted by the wind that they include chinstraps that suggest a football helmet for the home gardener. I have no interest in strangling myself while I hike, and so I have no interest in bucket hats or sunhats.

You Can Wear a Sun Cap with a Neck Cape, but…

Sun caps are totally fine, especially if having or expressing a personality just isn’t that important to you. That’s OK! They’re lightweight, breathable, and totally bland, the hat equivalent of having a thankless 9-to-5 job that you settled into because your parents told you that your passion would never turn a profit. If you love suncaps and want to express yourself as, say, a furry who loves rabbits, add one of those capes that drape down like leporine ears. You’ll look great, and thanks in advance for the laughs.

You Could Wear a Visor, but…

Seriously, though, what is wrong with you? Do you want your scalp to be sunburnt? Are you so ultralight that you’ve forsaken the cap part of your cap, or do you just want to look like Scott Jurek setting an FKT? Look, visors are good if you’re playing golf, but I’m just saying that because I don’t know enough about that tax-shelters-as-sport to disagree. Seems debatable.

You Could Wear a Headwrap, but…

As previously mentioned, I’m a middle-aged white dude with thinning and (goddammit) graying hair but without, well, a god. There are religious, cultural, and phenotypic reasons for all kinds of head wraps that will never apply to me; if they apply to you, amazing. But during those hatless days after the deer swiped my gear, I did try to use a Buff and even a bandana on my dome. I hated it—hot, sticky, damp, dirty. It’s just not for me, but I respect the headwrap’s minimalism and versatility, no matter what form it takes.

Bottom Line: Nothing Beats a Baseball Hat

Just think about it: For hiking, the baseball cap takes the virtues of everything I’ve mentioned and eliminates their concomitant problems. It offers the front shade of the bucket or the sunhat while giving you a plastic band in the rear for looping a bandana or a Buff if you’re worried about the back of your neck. When it’s wet, it still acts as a little umbrella, keeping the rain out of your face, and a cheap cap with holes or a little webbing at the side is breathable enough. It’s not much heavier than a visor or a wrap, and if you don’t want it on, it’s small and collapsible enough to be stuffed into any empty corner of space you have when you switch to your cold-weather knit cap or your Ray Jardine-designed beanie. If you need more sun protection, you should be always hiking with sunglasses, anyway.

And above all, it can say anything you want, from silly jokes that may help you find your friends on trail to the name of some favorite hang back home that reminds you of what awaits when the journey is done, like a daily postcard from the rest of your life. They’re cheap, ubiquitous, and totally easy to buy secondhand. If, say, a deer eats your prized selection because the salt on it was so good, you can find at least some sort of replacement at the next town you encounter. And by the way, if you ever see a dear wearing a Gunner hat near the Oregon border, thank it for the laughs.

Thanks to Crusher for the trail name and reminding me how important hats are as he begins his Continental Divide Trail hike.