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If the mainstream’s recent embrace of cowboycore has taught us anything, it’s that you don’t have to go full Costner cosplay to capture some of the hardened allure of western wear. It helps, of course, if you really know how to wear cowboy boots.
That’s one way to dip a toe into the movement: a pair of the official state footwear of Texas. Evolved from the equestrian boots popularized in Spain and Mexico, with a slim toe and raised heel meant to slide in and out of the stirrups of a saddle, the first American cowboy boots are believed to have originated in Texas or Kansas in the late 1800s, around the same time Levi Strauss and Jacob Davis were stitching together their first pair of blue jeans a few states westward. Apple, meet pie.
But finishing off a Canadian Tuxedo isn’t the only way to wear cowboy boots. Here's how to wear cowboy boots right, according to style icons like Pharrell Williams, Billy Bob Thornton, and Ralph Lauren.
Keep Things (Mostly) Classic
Pairing tan leather and blue denim is a sure win, but don’t be afraid to break tradition above the belt with a more of-the-moment coat. Nobody city slicks quite like Pharrell.
Tie One On
Think you can't dress up western wear? Think again. Ralph's natty tie and elegant wide trousers beautifully offset the ruggedness of his denim shirt and buckled boots.
Go Bold
Billy Bob demonstrated how to pattern mix snakeskin and pinstripes at the Original Sin premiere in Los Angeles a quarter century ago. It’s still a vibe.
Black 'Em Out
There's perhaps no combination more unimpeachably badass than a pair of slick black cowboy boots worn with sharp black trousers. You can keep things more casual up top, like Merle does here with his swaggering suede jacket, or you can just as easily go formal with a crisp dress shirt, tie, and blazer.
Mix and Match
The trick to making a Canadian Tuxedo and cowboy boots feel less cliché is to surround ‘em with less expected staples, like Yoakam’s imposing topcoat and stark white button-up.
Embrace the Zipper
If you avoid cowboy boots because of the struggle to get them on, a pair with a subtle side zip can change that. Look for ones where the zipper is the same color as the leather so they blend in.
Freak It
Don’t expect to find a rancher in Montana wearing his cowboy boots with baggy shorts, but A$AP Ferg makes the unlikely pairing work alongside a killer motorcycle jacket.
Our Favorite Cowboy Boots
Saddle up, pardner. Here are four classic pairs of cowboy boots we love—and don't miss our full list of all the very best options on the market.
How to Wear Cowboy Boots FAQ
Who makes the best cowboy boots?
We're fans of a whole host of cowboy boot brands here at GQ, from DTC upstarts like Tecovas to real-deal rodeo favorites like Ariat. But as far as the pound-for-pound, budget-is-no-concern best boots around, there's no denying the quality of storied Texas maker Lucchese. Renowned for their gorgeous leathers and wild detailing (usually with prices to match), Lucchese has been hand-tooling the preferred cowboy boots for the rich, powerful, and obsessively stylish since 1883.
How should cowboy boots fit?
Cowboy boots demand to be broken in. You want them to fit a touch snug at first, because the leather will lengthen and soften over time. When shopping for a pair of cowboy boots, look for contact on the top of your foot—at the instep and vamp—that will keep your heel in place even after it stretches a bit.
How do you stretch cowboy boots?
The only way to stretch leather is with time and force. It’s always a good idea to double up the socks and stomp around the house to avoid the first-wear blisters, but also consider a chemical assist in loosening and softening from a balm like Saphir Pommadier Cream or an instep stretching device to create a bit of room at the ankle.
What socks should I wear with cowboy boots?
It’s the boot doing the talking here, so wear socks that can handle the walking. You want something comfortable and breathable (a cotton blend is probably your best bet), that's also long enough to cover the calf and won’t slip and end up bunched at toe.
What are the best jeans to wear with cowboy boots?
While the mainstream’s standards have widened over the years like the flared leg on Pharrell’s Louis Vuitton denim pants, the title of “best jeans to wear with cowboy boots” has got to go to the original. Levi’s created the 517 Bootcut in 1969, specifically flared to be paired with the higher shaft of western footwear. They rode hard in the ’70s and are officially back in the saddle today.