by Igrew up in Texas and have lived in New York for the past seven years, so I’ve seen the full spectrum of how people wear cowboy boots. I write about Westernwear a lot—like, a lot— and with the revival of the trend this year, I’ve been seeing more cowboy boots than ever.
Sometimes, they’re styled in a traditional way, like the folks back in Houston used to wear. Sometimes, it’s a little bit more bold and contemporary. There’s no shortage of fashion guys in Lower Manhattan who are ready to whip out their Luccheses for happy hour in Dimes Square.
Whichever way you look at it, we’re right in the middle of a Renaissance of the cowboy boot, and you’ve gotta be ready for it. If you’ve recently secured a pair and are relatively new to the world of cowboy boots, or if you’ve had ’em for a while and are just looking for some fashion-forward styling tips, you’ve come to the right place. Saddle up for a masterclass in what to wear with your cowboy boots.
jump to:
- The Every and Any Way
- The Casual Way
- The Cool Way
- The Elevated Way
The Every and Any Way
When you live in Texas, you learn something about cowboy boots: they’re an everyday shoe. If you go down South, to where cowboy boots herald from, you’ll quickly notice that people wear cowboy boots with everything and anything. They’re as interchangeable and wearable as a pair of sneakers.
When I was in high school, guys would wear cowboy boots on the daily, with everything from jeans to cargo pants. Now, I’ll tell you this much—can and should are different. Yes, you can throw boots on with anything, butthat doesn’t mean everything looks equally good when worn with cowboy boots.
I’m about to take you into some of the best ways to style them, but before I do, you should feel absolutely free to experiment with your boots and style them however you want to. The only rule, to avoid looking too TikTok cowboy-core, is wear your boots under your pants, never over. They’re a lot more versatile and wearable than you might think; have fun with it, play around with some different outfits. You don’t have to lean into a fully-Western fit to pull them off.
Cowboy boots are meant to last you for years and years and years, and that includes all the different trend cycles that’ll pass you by in that time. They’re timeless, and very adaptable to your style. Throw on a graphic tee or a flannel button-down, a denim jacket or a blazer, and see what happens.
Shop Our Favorite Cowboy Boots
Tecovas Garrett Boots
Lucchese San Antonio Boots
RRL Plainview Roughout Suede Boots
Thursday Boot Company Desperado Boots
Frye Bruce Pull On Boots
Ariat Ridin High Western Boots
The Casual Way
The most classic, obvious way to style your cowboy boots? Bootcut jeans, of course. You really can’t go wrong with a slight flare in your denim; it doesn’t have to be anything crazy, but just enough space to fit the boot underneath your jean is perfect.
This silhouette is timeless (and recently had a major moment at the Super Bowl, thanks to Kendrick Lamar), and gives you a lot of room to play with what you wear on top. A button-down and belt is always a great bet; you can go for anything from a flannel to a proper Oxford shirt. A tee and a jacket or cardigan is another great silhouette. If you want to lean into the Western look a little bit, throw on a waxed trucker jacket and a baseball cap.
Keep in mind that most cowboy boots have a slight heel to them, so tucking your shirt into your pants will help elongate your legs further and make you look taller. You don’t have to tuck your shirt in, by any means, but having a decent belt on-hand, along with one or two shirts that you know look good tucked in, is a great move. Just remember that the color of your belt should probably match the color of your boots—the material as well, if you’re a traditionalist—to tie everything together.
Shop Our Favorite Casual Bootcut Jeans
Abercrombie & Fitch Western Straight Jeans
Todd Snyder Western Cut Jeans
Levi’s 517 Boot Cut Jeans
Wrangler Cowboy Cut Original Fit Jeans
The Cool Way
If you’re a little bit more on-trend, your closet is probably less bootcut jeans, more baggy jeans. Luckily, the latter still pairs nicely with cowboy boots.
I recently wrote a story advising you on what kind of shoes to wear with your baggy jeans, and both boots and pointed-toe shoes made the cut. You know what typically falls into both of those categories? You guessed it—cowboy boots!
Essentially, having a pointed toe and a slight heel at the end of your boot sharpens up your silhouette. It makes your casual fit look more intentional, and because baggy jeans tend to have the effect of making you look shorter, having that slight boost on your foot definitely helps elongate your form. Plus, it’s an easy way to offer something unexpected. A baggy jean and a sneaker will never look bad, but a baggy jean and a cowboy boot can look actively good.
There’s some room to play with what you wear on top here, too. A tee or tank with a jacket or cardigan isn’t a bad option, especially if you’re going for a boxy bomber or a sleek leather jacket. You can even get away with a hoodie, or throw a blazer over one to elevate it a little bit more. And speaking of elevating your fit—you should get into dressing up your cowboy boots, too.
Shop Our Favorite Cool Baggy Jeans
Gap Baggy Jeans
Todd Snyder Relaxed Selvedge Jeans
Everlane ’90s Loose Straight Jeans
Agolde Fusion Baggy Jeans
The Elevated Way
Yes, you can dress up your cowboy boots. Ask any of the boys I went to high school with what footwear they wore to senior prom.
In a number of cases, your cowboy boots can be suitable alternatives to loafers, derbies, or even Oxfords, at times. A pleated pant or a dress pant is a great silhouette to pair with your boots; the straight leg (and I do say to go for a straight leg, rather than a slim one) nicely complements the shape of the boot.
Your cowboy boots may look out of place with a full suit (not to mention a tux), but a dressy pair of pants and a simple sweater, or a tee and blazer combo, or even button-down and cool jacket should do the trick. If you want to lean into the casualness of the boot a little bit more, throw on a baseball cap, too. If you want to keep things elevated, go for a leather belt and a tie.
Shop Our Favorite Elevated Dress Pants
Madewell Relaxed Straight Workwear Pants
Huckberry Pleated Chinos
Banana Republic Signature Italian Hopsack Wide-Leg Pants
