20 Best Dresses To Wear With Cowboy Boots For Women

Channel the wild west and walk the land like you own it in the most apt dresses for these boots.

Reviewed by Paola Farina, Personal Stylist
Written by Pratima Ati
Edited by Madhumati Chowdhury
Fact-checked by Srijani Roy Chowdhury, Certified In Makeup Artistry, Certified Style & Image Consultant  • 

Staple footwear for the cowboys back in the 1900s, cowboy boots are no longer just a thing of the past. They are here, making the buzz in the fashion world for all the right reasons. Knowing this, we want to help you pick the dresses to wear with cowboy boots as you will never go wrong wearing this timeless footwear. Below are some innovative ways that you can try to rock these shoes like never before. All you have to do is, scroll down to see different cowboy boots for women and how to style them.

protip_icon Ace The Look
  • Color Combinations: A black pair of boots match every outfit color. Brown cowboy boots look perfect with grey and blue shaded outfits whereas tan ones work well with light-colored outfits.
  • Hairstyle: Go for French braids, loosely tied hair, beachy waves, or bouncy curls for a classy look.
  • Accessories: Some classy boot chains, bootstraps, tip toes, or boot bracelets can add more charm to your cowboy boots.
  • Maintenance: Brush off dirt every time you step out with your cowboy boots. Clean them with a leather cleaner every 2-3 months for longevity.

Best Outfits With Cowboy Boots

Paola Farina, a personal stylist, says, “Cowboy boots (Texanos) are a masterpiece for every closet. Dare with bold colors and decorations – the more, the better!” And you don’t need to necessarily buy them from a store. Farina says, “You can even order online, just select your favorite model and send them all the info about your foot size, length, and width, and they will be able to make the perfect-fit model just for you!” Here are some inspirational looks for you.

1. Shorts And Cowboy Boots

Shorts and cowboy boots
Image: Shutterstock

Wearing shorts, a crop top, shirt or a bralette with cowboy boots is an age-old style that won’t go out of style. Throw in a hat too, and you’ll complete the look.

2. Printed Jeggings And Cowboy Boots

Image: Instagram

Come winter or fall; we start living in our leggings, jeggings and all kinds of it. Make your outfit exciting one of these days by pairing them with cowboy boots. Underplay everything else, and let the boots take over.

3. Skinny Jeans And Cowboy Boots

Image: Shutterstock

Skinny jeans are yet another opportunity for you to flaunt your outfits with cowboy boots. Next time around, swap your ankle length boots or knee-high ones with these. Plaid and flannel shirts are a perfect fit for this outfit.

4. Boho Style One Piece And Pink Cowboy Boots

Image: Instagram

If you are headed to Coachella this year, or a similar concert, this look is perfect. A boho style one-piece dress with floral embroidery and tassels, paired with cowboy boots is a statement in itself. Just make sure these are comfortable though, because you are going to be doing a lot of walking and standing.

5. Floral Skirts And Cowboy Boots

Image: Shutterstock

How do you get attention to your feminine floral skirt and plain top outfit? Add statement pieces, in this case; you guessed it right, the cowboy boots.

6. Mom Jeans And Cowboy Boots

Woman wearing mom jeans with boots
Image: Shutterstock

Bootcut or mom jeans fit the cowgirl aesthetics perfectly. A plain shirt tucked into your mommy pants with cowboy boots, and a hat, will all align themselves to the theme like nothing else ever did.

7. Bridal Wear And Cowboy Boots

A bride wearing cowboy boots
Image: Shutterstock

The country theme has become increasingly popular for weddings, and people are not shying away from the idea of sporting boots with their cocktail or bridesmaids dresses. After all, marriages are a celebration and for you to have fun. It’s a fun idea, and it’s not every day that you get to do something this fun.

protip_icon Stylecraze Says
Stick to rustic style dresses and dresses in lighter fabrics or lace to go with your cowboy boots. Large traditional ball gowns may not be the greatest choice for this look.

8. Denim Or Corduroy Overalls With Cowboy Boots

Image: Instagram

You can pull off your overalls to match the millennial trends, or time travel like you belong to the 70s. If you feel like doing the latter, do that with denim, or even better if it’s corduroy overalls, and finish it with boots.

9. Floral Dresses And Cowboy Boots

Image: Shutterstock

Bring in a slice of Texas or Nashville into your outfits in a floral one-piece dress and cowboy boots. Add a hat, and you need no other accessory.

10. Knee Length Summer Dress And Cowboy Boots

Image: Shutterstock

I know cowboy boots are not a summer staple, but why not? On days when it’s not boiling outside, and you are in a mood to try something different, go for it. Either way, cowboy boots are not for every day. Make summers fun with strikingly different looks each day.

11. Strapless Lace Dress And Cowboy Boots

Image: Shutterstock

Match this delicate lace dress with a pair of cowboy boots, just like Serena Williams, who loves sporting her tennis shoes with just about everything.

12. Off-Shoulder Dress With Cowboy Boots

Image: Instagram

Off-shoulders have been the pattern of the season. From dresses, maxis, to bridal wear and tops – everything is a hit. If you are passionate about trying all of them, work a skirt or a top with cowboy boots.

13. Vintage One Piece With Cowboy Boots

Image: Instagram

Did you get an invite for a vintage or country-themed party? Check this outfit that screams country. And it’s so easy to pull this look off. Gather a vintage dress, and pull your cowboy boots out; wear a hat or tie up your hair in a bandana; wear a tote bag and strut around looking like a diva from yesteryears.

14. Denim Skirt And Cowboy Boots

Image: Instagram

A denim skirt is yet another opportunity for you to look like a Southern diva. The next time you are headed to the Smoky Mountains, or someplace down South, carry a pair of these boots or buy one from there and act as you belong.

15. Asymmetrical Dress With Cowboy Boots

Image: Instagram

Pairing a comfortable white noodle strap dress with cowboy boots is not the first thing that comes to our mind, but why not? Wear fine jewelry, neutral makeup and style your hair in beachy waves – boho chic in the most real sense.

16. Frayed Shorts And Cowboy Boots

Image: Instagram

Frayed anything means that you are setting a casual chic vibe to your outfit. Pair it with a graphic T-shirt and cowboy boots for good measure.

17. Black One Piece With Cowboy Boots

Image: Instagram

Remember how we spoke about vintage and country becoming a theme for weddings? If you received an invite for a wedding on similar grounds, the easiest way to keep up with it is to finish your look with cowboy boots. Even otherwise, give this a shot.

18. Yellow Dress And Cowboy Boots

Image: Instagram

What can I say? Wear a yellow shirt dress and throw in cowboy boots to instantly spruce up your look.

protip_icon Stylecraze Says
Since yellow is a vibrant color, it is advisable to match a yellow dress and cowboy boots with neutral accessories in colors like white, black, tan, navy, or brown.

19. Turquoise Outfit And Cowboy Boots

Image: Instagram

If you haven’t heard of it already, turquoise outfits with cowboy boots are a thing. Pair it with a suede or leather skirt, jacket with floral embroidery, old-school sunglasses, and a high ponytail. Cannot get better than this, can it?

20. Joggers And Cowboy Boots

Image: Instagram

Who would have thought that joggers can be combined with cowboy boots? So the question here is not why, but why not! In today’s world of fashion, you can style your outfits any way you like as long as they are not outlandish or OTT. Actually, that’s fine too, if you can do it with confidence.

Infographic: 6 Cute Outfits To Pair With Cowboy Boots

Don’t consider this classic a thing of the past. Cowboy boots are here to jazz up for style. But too many options can be overwhelming. While you can pair the boots with any outfit, some combos look ultra-stylish, no matter what. The infographic below contains the top outfit combinations that complement cowboy boots. Scroll down to check it out.

6 cute outfits to pair with cowboy boots (infographic)

Illustration: StyleCraze Design Team

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Download Infographic in PDF version Download Infographic
Download Infographic in PDF version

With the above ideas on how to style outfits and dresses with cowboy boots, you can now flaunt them with confidence. Whether its shorts, floral skirts, or bohemian or maxi dresses, style your outfit as per your occasion and preferences and make those cowboy boots a style statement. Fashionable, stylish, and comfortable, follow the above ideas to rock this retro look.

Frequently Asked Questions

How do you dress stylishly in cowboy boots?

Accessories like a decorative belt, bandana, and hat can help you achieve a stylish look with cowboy boots.

What should you not wear with cowboy boots?

Cowboy boots are a bold fashion piece, and you can experiment and have fun with all kinds of dresses on them. However, avoid wearing them with overalls, prairie dresses, athleisure, sequins, and fringes.

Should I tuck my jeans into my cowboy boots?

If you wear skinny jeans or slim-fit leggings, you can tuck them into your cowboy boots. However, if your pants are wide-legged, it is better to let them go over the top of your shoes.

Key Takeaways

  • Cowboy boots with a flowy maxi dress for a bohemian-chic look.
  • Cotton or linen attire and pair with brown or tan cowboy boots for a classic Western vibe.
  • For a casual look, add a layer of denim shirtdress with denim pants or shorts with a pair of brown or black cowboy boots.
  • More than anything, try to accentuate your own style to suit the occasion.

Discover the ultimate guide to rocking cowgirl boots with flair from the following video! Unleash your inner rodeo queen by delving into stylish pairings, accessorizing tips, and boot care essentials.

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