How to Wear Cowboy Boots—9 Outfit Ideas to Try

This outfit features a tailored vest to add a fashionable twist to the classic cowboy boots and denim cutoffs look that has been around forever. Adding longer denim shorts helps highlight recent trends for Bermuda shorts, and it helps avoid any unintentional Daisy-Duke vibes, too.

When shopping for the pieces for this outfit, start with a pair of classic, neutral colored cowboy boots like this two-tone pair from Mango. Next, look for some loose, broken-in Bermuda shorts, similar to the ones you can find with our . Finally, finish off the look with a sleek, fitted vest. We love the look of The Tailored Vest in stretch cotton on its own or layered over a fitted tee or tank.

When you’re ready to shop, use our Mango promo code for the best price on your new boots. (Image credit: @rebellemj)

By combining a tweed jacket, fitted pants, and boots, you achieve a look that's reminiscent of a classic riding outfit yet has a subtle Western edge. It works especially well with dressier pairs of tall boots in a solid color with a glossy finish. This polished yet fun look is great for a brunch or casual Friday at the office.

This outfit benefits from stocking up on some iconic wardrobe essentials. With our J.Crew Factory promo code, you can get a solid pair of white skinny jeans that will work with a variety of cowboy boot looks. For a jacket, consider browsing Ann Taylor's wide selection—we love this pink tweed version for a feminine take—and using our Ann Taylor promo code to save. To ensure the look remains sophisticated, opt for a darker pair of boots in a rich brown or deep black. 

Need a cozy, casual look for running errands or game night? You can’t go wrong with cropped jeans, a soft sweater, and a great pair of cowboy boots. This effortless combo works especially well with boots that have a shorter shaft and a bit of extra flair—think embroidery, fringe, or fun stitching that will peek out under ankle jeans.

Start with a light-wash pair of cropped jeans (we love the selection at Gap). Not only do they offer multiple inseam options to help you find your perfect fit, but you can also save with our current Gap promo code. Top it off with a Merino wool sweater from UNIQLO—they’re ultra-soft, versatile, and great for layering. Don’t forget to snag one using our UNIQLO coupon. (Image credit: @whatabbeywore)

This look is a stylish blend of boho charm and Western edge. A lightweight shirt dress brings a feminine, breezy feel, while structured cowboy booties add a grounded, casual finish. It’s the perfect pairing when you want something easy to throw on but still polished enough for brunch or a weekend outing.

We recommend going for ankle-height booties with a block or stacked heel—DSW has plenty of great options, and you can save with our DSW coupon. To play up the Western aesthetic, try a gingham print. Prefer something more relaxed and bohemian? Opt for a flowy dress from Anthropologie (and don’t forget to use our Anthropologie promo code). For a final touch, add a wide-brimmed hat or a leather belt to tie the look together. (Image credit: @_heyitsheidi__)

If you're into romantic, whimsical outfits, this one’s for you. Pairing cowboy boots with a flowy lace or floral skirt creates a soft, feminine vibe with just the right amount of Western edge—perfect for date night, concerts, or an evening out.

To pull it off, choose a skirt that drapes just over the tops of your boots for a cohesive, layered look. We love this lacy option from Lulus (made even better with a Lulus promo code). You can’t go wrong with just about any top, from vests to vintage tees. Finish the outfit with a bold, Western-inspired belt to tie everything together and echo the details of your boots. (Image credit: @sarah_lutz_)

Want a look that leans more rocker than rodeo? Pair your cowboy boots with distressed jeans and a leather jacket for a look with plenty of edge. This combo tones down the Western feel while adding plenty of street-style cred.

When choosing your jeans, aim for a relaxed, classic fit—not too tight, not too loose. We love Levi’s 501s for their timeless cut and lived-in feel. As for the jacket, go for one that complements your boots without competing with them—something sleek with a bit of grit. This pick from Macy’s nails the look (and you can save with our Macy’s promo code). We’re all about a bold, tall Western boot to top off this look—white or off-white styles create an eye-catching contrast and earn bonus points for their versatility. (Image credit: @nataliebertolone)

Cowboy boots have a very soft, charming look when paired with a long, floral dress. This outfit boasts a prairie-chic vibe that is perfect for a summer festival, a spring picnic, or any other outdoor event. It lets you show off boots with embroidery or other whimsical elements while still maintaining a casual and cute look.

This look is all about finding the right dress, so shop carefully. Reformation is a go-to for gorgeous, flowy styles—and you can score one for less with our Reformation promo code. To complete the outfit, top it off with a simple, wide-brim hat like this one from Free People. It adds a relaxed, polished touch without overwhelming the look and is on discount with a Free People promo code. (Image credit: @miamistylemom)

Love the charm of floral dresses but want something with a little more edge? This look has your name on it. A breezy, flowy blouse brings softness, while a leather skirt adds a rebellious, flirty twist. It’s one of our favorite ways to style cowboy boots for a day-to-night outfit that feels cool and put together.

To make this combo work, it’s all about balancing proportions. A fitted skirt—like the Madewell Suede Mini—pairs perfectly with the relaxed silhouette of a blouse. And don’t sleep on the power of a tall Western boot, like these Corral Women’s Boots, to anchor the look and complement the shorter hemline. (Image credit: @styleherstrong)

If you’re after a modern, elevated way to wear cowboy boots, this outfit is a winner. A fitted blazer and a denim midi skirt set a sleek, structured foundation—perfect for letting a bold pair of boots steal the spotlight. It’s the kind of look that feels fresh and polished while still having a playful twist.

Since the boots are the star here, go all in with a metallic pair like the DV Dolce Vita style you can snag at Macy’s. When it comes to your skirt and blazer, fit matters. A more tailored blazer keeps things sharp, while a denim midi with or without a slit lets your standout boots take center stage. Find an array of blazers in sleek, neutral tones at J.Crew and use a J.Crew promo code at checkout to get this staple piece for less. (Image credit: @amandarejon)