The joys of looking ridiculous

Or when you're required to wear a cowboy hat, you know it's a good assignment

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Burpee update: I have given up in my attempt to continue MABA (Make America Burpee Again) all year. Normally MABA is 100 burpees per day in January; I tried — unsuccessfully, it turns out — to extend it for all of 2023. I hurt my back/hip after 14,188 and I’ve barely done any since. I’m 50 percent sad to be unable to reach a completely stupid and utterly pointless goal, 50 percent glad to be done, and 50 percent relieved I didn’t hurt myself even worse.

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The greatest cowboy hat story ever told

In pursuit of stories I’ve had to wear …
Bowling shoes

Golf shoes

Rock climbing shoes

Running shoes

Biking shoes

Water shoes

Hiking boots

Skiing boots

Winter boots

Monster Alaska winter boots (twice)

Snowboarding boots

Crampons

Life jacket

Flyfishing waders

Hiking hat

Sunglasses

Eye protection

Ear protection

Helmets for biking, rock climbing, ice climbing, tree climbing, rapelling and more

Kevlar vest

And probably a lot more I’m forgetting. I never wrote about any of those.

But last summer, in order to fulfill an assignment, I was required to wear a cowboy hat.

Yes, required.

So of course I wrote about that because once I put it on I looked like a total dork. Even now, when I wear it, my wife gives me that look. You know the look. It says I love you even in that fool thing which you should never wear in my presence again.

Here’s the story, which appears in the latest issue of Mountain Outlaw magazine.

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Dust dances in the rodeo arena in front of me as a parade of livestock marches toward the chutes. Behind me, kids in the bleachers stuff themselves with cotton candy and Western-clad adults swig ice cold beers. I stare intently at the bulls and the men atop them, the co-stars of this portion of that unequaled celebration that is Cheyenne Frontier Days.

As one cowboy after another gets bucked, I have an uneasy feeling that everyone is staring at me. Or more to the point, staring at my hat. My cowboy hat. It’s the first one I’ve ever owned, and this is the first day I’ve ever worn it. As I lean against the railing, I feel like I’m standing under a giant neon sign that says POSEUR with an arrow pointed toward my head garment. 

I had long planned to take advantage of my media pass and go behind the scenes at the rodeo, but to do so I needed a cowboy hat. I mean that literally: the Professional Rodeo Cowboys Association requires anyone who will be anywhere they might end up on TV to wear Western clothing. That means a Western shirt, jeans, cowboy boots, and yes—a cowboy hat.

This was not my first rodeo, but it was the first time I’d encountered the dress code. I had jeans on, my shirt was sufficiently Western to pass the eye test and apparently nobody noticed my blue Saucony running shoes. But my naked head was a glaring infraction that needed to be covered. So before the rodeo, Andi Jaspersen, the extraordinarily patient Visit Cheyenne representative assigned to make my trip one to remember, shuffled me over to The Wrangler, a cowboy hat store in downtown Cheyenne, so I could get fitted for my very first cowboy hat.

I’ve lived in the Midwest, South and East and had never been to—nor even heard of—a cowboy hat store. As it turns out, this is a significant moment in a man’s life, especially a man who’s never owned and barely worn a cowboy hat. I walked up and down the aisle, looking for the perfect lid, something that said: I don’t look ridiculous in this at all, in fact I feel completely comfortable with it on.

Not a single one said anything like that.

I asked a salesman for help. I told him I wanted a hat that would keep the sun off my face and neck. Upon later research, I realized I had asked for a cowboy hat that did exactly what cowboy hats were invented to do. Next up: going to the glove store to ask if they have anything that will keep my hands warm.

I smushed a few hats onto my head. The one sized 7 5/8ths felt right.

“How do I know if it fits?” I asked.

“Go like this,” the salesman said, plucking the brim with his finger. I plucked it. It didn’t budge. It fits, I supposed. Another employee steamed my selection then bent it to fit it to my face. I thought the whole process might be a con, and I suspect they might still be laughing about how the dope from St. Louis fell for the steaming bit. But I went along with it. The salesman placed the hat gently on my head, adjusted it just so and declared me ready for my debut.

It took one peek at my reflection for me to sorely disagree. I looked in the mirror … and saw a fraud.

Y’all out West are friendly as can be—and terrible liars.

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This year’s Cheyenne Frontier Days will be the 127^th. It will bring in approximately $40 million in revenue spent by roughly half a million visitors, and just about all of them will be wearing cowboy hats.

I learned from talking to cowboys and cowgirls in Cheyenne that a cowboy hat symbolizes a hard-earned outlook on life, a devotion to rugged individualism. The best cowboy hat is a perfectly fitted (and immaculately steamed) (allegedly) declaration that you can stand on your own two feet and look good doing it. A cowboy hat connotes confidence but not arrogance, humility but not acquiescence, a calm patience and understanding that things will work out for the best—and you’ll figure it out if they don’t.

“Everybody that’s wearing these hats are doing an homage to a lifestyle that actually made this part of the country what it is today,” said Mike Kassel, associate director and curator of collections at the Cheyenne Frontier Days Old West Museum, one of many places to which I wore my new hat.

He’s right about the homage, and the reason I felt unworthy of my hat is I have nothing to do with that lifestyle. I mean, I can ride a horse so long as it doesn’t run. Or trot. Really I prefer it if they don’t move at all.

At the rodeo one glorious afternoon, I sat next to Cheyenne Mayor Patrick Collins. On this outing, he donned one of his three cowboy hats. This one was made of straw (like mine) because no self-respecting cowboy wears anything but straw outside at a rodeo in the summer (or so I’m told).

“When I see cowboys, I think really highly of that species of people,” Collins said. “They’re the hardest working, straightest-shooting kind of guys. To be considered in that category, for me, would be an honor.”

Collins looked like he was born in his hat, so I was shocked to learn he too was a newbie to cowboy hats, even though he’s lived in Cheyenne since the 1970s. When he finally bought one a few years ago, he went through an extensive fitting process for a hat made of beaver. When he put it on, he had the same reaction I did: “I feel like I’m in a costume. But I can’t tell you how much I look forward to doing it now,” he said. “It just feels right.”

Yee-haw! Maybe there was hope I would eventually grow into mine, too. But that afternoon, I still looked like a teenager with peach fuzz who thinks he needs to shave. In this region that so values authenticity, surely everyone saw right through me. I wanted to take it off. I kept wearing it only because Jaspersen and others told me I looked fine.

As I mentioned: Y’all out West are friendly as can be and terrible liars.

As it turns out, my own process of fitting in to the cowboy hat mirrored Cheyenne’s. Western gear wasn’t always de rigeur at Frontier Days. For the first 20 years or so, locals wore “normal” clothes to the festival, according to Kassel. “Even some of the cowboys would be wearing shirts, ties and blazers,” he said. “You wouldn’t think you’d see someone in a nice Windsor knot getting on top of a bucking bronc and having a good time. But it did happen.”

During the late 1910s and early 1920s, Wyoming went into a depression a decade before the rest of the country. Looking for a way to lure tourists (and their money) to Cheyenne, city leaders embraced the popularity of movie Westerns. They put out a call to locals to dress like they were going to appear on the big screen. “It became really popular,” Kassel said.

Flash forward more than 100 years, and cowboy hats are the unofficial uniform of Frontier Days.

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I love to travel because I get stretched and pulled. I learn from the culture wherever I go. I study how people live, love and work. When I return home, I’m stronger, like a cowboy hat that never loses its shape no matter how many horses trample it.

The days I spent in Cheyenne observing cowboys and cowgirls and talking to them about their cowboy hats, I was reminded that the true spirit of the cowboy, while symbolized by the hat, far transcends any attire. Those days reminded me that hard work brings joy in and of itself. They reminded me to celebrate early mornings, hard days and memorable nights. And they reminded me of the value of chivalry and honor, of telling hard truths, and of getting back on the horse no matter how many times you fall off.

With these lessons retained under my new garment, I kept the hat on. After wearing it to the rodeo, to the Old-Fashioned Melodrama at the Historic Atlas Theater, for steak at the Wyoming Rib & Chop House and downtown to the biggest pancake breakfast I’ve ever seen, I started to feel comfortable. A few days in, I forgot it was there; the hat became part of me.

I am western, I am free, I am a cowboy! I thought. I suppose I could’ve pulled that off, too, if I didn’t bang it into the car door every time I tried to get in.