'Win or Lose' Regales with a History Lesson on Cowboy Hats

April 09, 2025

'Win or Lose' Regales with a History Lesson on Cowboy Hats

Tourists often visit our Horseshoe Quarter Circle ranch. Of course, us horses are the main attraction! Horses are herd animals by instinct. Several of us run together in the same pasture. One time, Twist, another horse in our pasture that has been here as long as I have, asked me, “Hey, have you ever wondered where cowboy hats came from?” I suppose he was prompted to wonder that because a bunch of dudes, wearing the craziest hats, were headed for us!

Tango, also one of our herd, answered, “Yeah, I know they're a big deal in the West, but what's the actual history behind them?”

Well, I'm Win or Lose, a seasoned horse who's seen more cowboy hats than you can shake a tail at. So, being the most opinionated and knowledgeable of all of us in this pasture I regaled them with a history lesson.

It all started with the Mexican vaqueros, you know, the cowboys before there were American cowboys. They wore these big sombreros for sun protection.

Twist chimed in, “Oh, like the ones you see in old Western movies?”

Exactly! But those American cowboy hats we think of today, got their big break thanks to a guy named John B. Stetson.

Tango mused, “Stetson... Sounds familiar. Didn't he make the classic cowboy hat?”

Bingo! In the 1860s, he made this hat called the "Boss of the Plains." It was perfect for the cowboys. Big brim, high crown, made from beaver felt. Super durable. 

Twist cocked his head, “That's pretty cool. So, it was all about practicality at first?”

Definitely. But then it became more than just practical. With Wild West shows and later movies, the cowboy hat became the symbol of the American West.

Today they are everywhere, from fashion runways to country music concerts.

Yeah, they've evolved a lot. Now you've got all sorts of styles - cattleman, gambler, even Cool Hand Luke, worn by bull riders.  And they're not just felt anymore; straw hats for summer are huge.

Tango mused, “It's wild how something so functional turned into such an iconic piece of culture.”

Totally. It's like wearing a piece of history on your head. Plus, there's just something about a cowboy hat that screams "adventure."

Twist nodded his head thinking, “I might need to get one now, just for the vibe!”

Do it! They're not just for cowboys anymore; they're for everyone who loves that spirit of freedom and the outdoors.

As time went on, hats became a common sight. Cowboys would tip their hats to each other as a sign of respect. A sign that said, "This cowboy knows his way around a horse, around the land." Win or Lose reminisced, “I felt proud, in a way, to have someone with a cowboy hat pick me out of the herd to ride."

Today Cowboy Hats are everywhere. They come in all shapes, some with fancy bands or feathers. They're not just about work anymore; they're about identity, celebration, and even fashion. I've seen people at shows and gatherings, all wearing these hats, and I must say, it does something to the spirit. Makes everyone feel a bit more like they belong to this vast, open world we horses love so much. And they've added this... flair to our partnership. It was like the crowning glory on the head of every cowboy that rode me.

As time trotted on, I saw those hats change. They got creased here, pinched there, turned into an iconic statement about the person wearing them, more than just a shield from the elements. But they never lost their charm, not to me. Each hat I see tells a story - of the cowboy or cowgirl, the rancher, or even the city folk who just love the feel of the West.

I've seen them at rodeos, where the sun beats down like a drum; I've seen 'em at weddings, where they're all dolled up, looking as fancy as a horse with a new saddle. And I've seen 'em in the movies, making legends out of men like John Wayne.

They come in all sorts of shapes and sizes, straw for when summer makes my coat too warm, felt when the winds start to chill. But to me, every cowboy hat is a reminder of long days on the trail, the bond between a horse and rider, and the spirit of the frontier that never really left us.

I might be called Win or Lose, but with a cowboy hat in sight, I always feel like we're winning at the game of life out here under the big sky of Montana.  Connolly Saddlery, established in 1912, knows all the history, they've been part of most of it! And they've kept up with the changes. American Hat Co. pretty much owns the hat market in the 21st century. Connolly’s has hundreds of hats on the floor for customers to choose from.  Expert hat shapers, Dave, Bo and Bill style every hat for each customer according to their personal taste and identity. Stop in to visit or give them a call! You'll be glad you did.  Tell them 'Win or Lose' sent you! 




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