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.

By Pratima Ati

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 and find them out. So go ahead.

Best Outfits With Cowboy Boots

1. Shorts And Cowboy Boots


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

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


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 shirts are a perfect fit for this outfit.

4. Boho Style One Piece And Pink Cowboy Boots

If you are headed to Coachella this year, or a similar concert, this look is perfect. A boho style one-piece dress 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


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

Bootcut or mom jeans go perfectly well with your cowboy boots. A plain round neck T-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

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.

8. Denim Or Corduroy Overalls With Cowboy Boots

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


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


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


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

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

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

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

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

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

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

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

19. Turquoise Outfit And Cowboy Boots

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

20. Joggers And Cowboy Boots

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.

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.

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After working in Marketing and Business Development for a few years, Pratima Ati jumped ship to pursue two things she... more