Blame John Wayne—or maybe it’s George Strait—but undoubtedly you’ve been chasing a sunset on a two-lane highway or bumping down a dirt road with the latest Chris Stapleton or Whiskey Myers on the radio and you’ve looked into the rearview mirror and thought, “fuck…I need a cowboy hat.”
If you’re from most parts of this country you’ve grown up around men in cowboy hats. They’re usually hardened, leather-tanned, blue-collar men we respect for their work ethic and their listen-first, speak-second philosophy. They’re timeless while also being a throwback. They’re what most of us think when we’re proud of where we’re from.
That’s my dad. A Vietnam veteran turned long-haul trucker who gave that up to become a mechanic and a father; but also the last of my family to be born on a farm in this country since the 16th century when he arrived in 1949 and moved us “into town” in 1985 after I was born.
His hands are hard, calloused and worn from 70 years of work. I’ve never seen him in a shirt that didn’t button from belly to chin and he’s sure as hell never worn skinny jeans. And while we have many style differences, as I passed 35 years old I found myself (and the rest of the world), starting to adopt some of the style classics of his generation.
Blue jeans made of real denim. Clothes that fit right and are made to be worked in and worn. Boots in every season. And hats. Especially cowboy hats.
It was a beautiful day in Jackson, Wyoming.
Walking around the town square we dipped into a western and outdoor men’s store to look for hiking gear. My dad, brother and I drift to the cowboy hats—something we’ve always joked about buying but never pulled the trigger on. Pop, in his subtle and subdued way, gets a small grin in on his face and says, “I bet you boys have never seen me in a cowboy hat.”
You see, Pop’s cowboy hat days faded away about the time he gave up driving produce from the Mexico line to the rest of the country. Mom, a transplant from Detroit, Michigan and more hippie than cowgirl, probably had a lot to do with this. When you grow up on Motown, Charlie Daniels isn’t really your vibe.
As he reached for a Stetson with a rich, tan felt and put it on, I decided I had to have one too. We left that outfitter with three cowboy hats and a new bond.
I wore mine all week.
There’s a feeling to saying “fuck it” and making a decision to do something you know your friends may mock. There’s something cowboy in buying a felt, curved hat and comfortably wearing it outside your quarantine quarters.
That’s a conversation I had last week after picking up a second cowboy hat and unveiling it at my son’s birthday party. Expecting jeers and some “what the fuck are you doing?” questions, my older brother pulled me aside.
“You know what’s the most cowboy thing you can do?,” he asked. I sipped my Coors Banquet with a shake of my head, waiting for big brother’s wisdom. “Wear the fucking hat and don’t care what anyone thinks. That’s cowboy. Also, it looks good”
He was right. He is right, the blessing of almost 43 years of lessons and a quiet confidence that means wearing what you want and not fitting in with the crowd. And that’s definitely cowboy. The confidence to walk into any room being unabashedly you—that’s cowboy.
In an age of social media and FaceTime, we’re all spending too much time wondering what everyone else thinks of us. We live in a society where we post outfits of the day not to show our confidence but to receive affirmation from strangers.
Give that up. Buy the fucking hat. And wear it. Because you do look good in that hat. And you can pull it off.
So whether you’re going for Clint Eastwood or Casey Dutton, grab a Stetson and a pair of Tecovas. You’ll quickly realize they work with everything you’re already (hopefully) wearing.
—Stetson JBS Heritage 6X Cowboy Hat ($235)
—Stetson Shasta 10X Premier Cowboy Hat ($395)
—Resistol 6X Cody Johnson The SP ($230)
Wear it with:
—Tecovas The Chance ($225)
—Tecovas The Shane ($245)
—Lucchese Majestic Roper ($395)