What to consider when styling cowboy boots:
The key is to avoid anything too costumey: leave the gingham skirts, chaps and Stetson hats at the ranch. But that doesn’t mean you can’t lean into the western theme: feel free to wear your cowboy boots with bootcut jeans, Canadian tuxedos (that’s double denim, just FYI) and even fringing. However, it needs to look elevated – so look for grown-up versions (need we go on more about Gabriela Hearst’s Autumn/Winter 2026 collection) of this every time, and you’ll be winning.
And if you’re not a cowgirl at heart? The easiest daytime wins look like a midaxi summer dress for instant chic. The Y2K-heads are wearing their cowboy boots with fairy-style skirts and tank tops, while the boyish and bold are plumping for bermuda shorts and a blazer. We’ll never not love the Saint Laurent-inspired glamour that is an LBD plus black western boots, though.
How should cowboy boots fit?
Traditionally, cowboy boots – like the kind we have featured from Ariat – don’t have the same fit as other shoes. They tend to be looser, slightly boxier, and tougher, rather than form-fitting and supple (it’s why they last so long). However, contemporary takes on the cowboy boot come in different fits; it all depends on the shoe’s design.
A sock style will sit as it should, close to the foot at the vamp and ankle, but the pointed toe may sit some way out from your actual toes. It’s always best to check the size and fit notes on a product page before ordering – ordering two sizes with the intention of returning one isn’t great for the environment.
Why you can trust me:
I am not ashamed to say that I am a fashion editor who has six pairs of cowboy boots sitting in my wardrobe as we speak: red and black Ariat pairs, a sassy silver number from Annie’s Ibiza X Terry De Havilland, white and black ankle pairs, as well as a cool mule style from #OldTopshop that I wore to a hen-do just last week. I am not ashamed because for all the reasons I have explained above – this shoe is timeless and goes with everything, not to mention many of these pairs have lasted me over five years and will no doubt go the distance. They are so worth the investment.
I am also a fashion expert with a decade’s experience in the industry writing for titles like WhoWhatWear, Red, Cosmopolitan, ELLE and Harper’s Bazaar. Obviously, as a footwear fanatic, I steer things towards shoes when I can; writing articles about the coolest footwear brands out there and creating round-ups of the best cowboy boots, platform sandals and clogs.
As part of my job, I am lucky enough to test plenty of products before they even hit the market. When I am not writing, I am flitting between press previews and events to discover the latest innovations in fashion and footwear, not to mention chatting to founders behind the best shoe brands. If I’m recommending something, it’s because I rate it. And I’m fussy AF.
For more from GLAMOUR UK’s Senior Commerce Writer Georgia Trodd, follow her on Instagram @georgiatrodd. For more from Glamour UK’s Freelance Contributor, Abigail Southan, follow her on Instagram @abigailsouthan.