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Greta Hollar

Nashville, TN

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How to Wear Cowboy Boots

January 23, 2026

This post about how to wear cowboy boots contains affiliate links.

If you’re visiting Nashville or even a local like me, you probably have at least one pair of cowboy boots. In Nashville, cowboy boots are more of a fashion statement, and the crazier your boots look the better! If I’m being honest, I’ve owned cowboy boots but didn’t start wearing them until this past year. Seychelles, Dolce Vita, and Jeffrey Campbell released styles that turned this fashion lover’s heart into a puddle and I’ve been wearing these fun styles ever since. Even when I was in New York for fashion week a lot of the street style I saw were fun ways to style cowboy boots. So today, I thought I’d share with you a few tips on how to style your beloved cowboy boots for women.

How to Wear Cowboy Boots

Watch Your Denim Length

Jeans and boots are two classic things and they’re great when worn together! You can wear your jeans over or under your boots but beware of the denim length. Skinny jeans are always an obvious choice because they can be tucked in any boot and look great. Straight-leg jeans might not fit over the boot and look bunchy when tucked in but would work with ankle boots. Cropped jeans are also a gamble because you don’t know how they’ll fall on the length of the boot. Wide flared-leg jeans might work as well if you’re not concerned about showing off your boots.

If you’re packing for a trip or planning an outfit, try your jeans on with your boots beforehand. Try several pairs and pick the cut jeans that make you feel the most confident and that look the best with your boots. You’ll find the right way after some trial and error. 

4 Fall Outfit Ideas from Abercrombie | Greta Hollar

Don’t Go Full Cowgirl If That’s Not Your Vibe

Yes, you’re wearing cowboy boots, but that doesn’t mean you have to go full cowgirl. Mix and match different styles and pieces. You could have leather boots or metallic or even velvet! You don’t have to wear denim, plaid, flannel, and fringe just because you have your boots on. I’ve styled boots with sundresses, skirts and a tee, shorts and a long-sleeved floral bodysuit, a black mini dress, a slip dress, and more! Cowboy boots are a favorite of mine to throw on with an especially feminine or fancier dress. Boots can make anything look more casual and effortless. 

How to Style Your Cowboy Boots | Greta Hollar
How to Style Your Cowboy Boots | Greta Hollar

Don’t Go Wild with Patterns and Colors

It takes a bold fashionista to rock cowboy boots and I salute you! But an easy way to mess up is to think it’s okay to wear patterned or over-the-top boots with an over-the-top outfit. Hear me out, if your boots are multi-colored and patterned, let the boots shine on their own. Pair a little black dress with your fabulous pattern or another neutral color (navy, brown, grey, beige, white, etc.) What’s the point of splurging on fab boots if your loud outfit doesn’t let them speak for themselves?! Also, we want you to look fresh out of Vogue, not fresh out of the circus.

Now if your boots are plain neutral like black cowboy boots or brown, feel free to dress them up with a bright patterned dress or midi skirt! The whole idea is to compliment the boots

How to Style Your Cowboy Boots | Greta Hollar

Dress It Up

While cowboy boots are seen as more casual shoes, dress them up! Throw on your oversized blazer and trench coat. Boots and suits are such an unexpected pairing. Mix and match textures too if you have a neutral colored boot on! Add ruffles, silk, satin, velvet, or leather for an elevated and polished finish that Vogue will want to copy. (Just don’t do sequins or fringe.)

Don’t Get Too Country On Me

While I have paired my overalls with cowboy boots before, do as I say and not as I do. Don’t go for the obvious fashion choices like denim, florals, and too Western. Grab an animal print or a sophisticated white button-up and blazer (very Ralph Lauren). Also, please don’t wear your cowboy boots with biker shorts or athleisure, it just doesn’t work. 

Many designers from Fendi to Isabel Marant are designing western boots so don’t worry friend, you are on-trend right now! The important thing is to make sure you’re comfortable and get the right size in your boots. Boots come in all sizes and widths so if you’re dropping a chunk of change, you can be picky about fit!

I’ve linked all my favorite Cowboy Boots Here!

Are cowboy boots on trend for 2026?

Yes, cowboy boots are still on trend and not going anywhere anytime soon.

Do you wear socks with cowboy boots?

100% yes! You need a protective barrier between you and the boots to absorb moisture and create a barrier to help with blisters.

Should you size up or down in cowboy boots?

Size up. Socks can add up to 1/2 a size if they’re thick and you want the boots to be comfortable and not too tight.

How do you style your cowboy boots? Share with me in a comment below!

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5 Comments / Filled Under: ., Style

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Comments

  1. Harry says

    January 30, 2023 at 3:30 am

    Amazing! I am happy to read this post because I read it and I get great information in this Article. I am blogger, I am writing and Article about Best water-proof leather boots. Your blog post is most relevant to me. I think you visitor happy to read my blog post and it may very helpful for them.
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  2. Blanks says

    May 9, 2023 at 11:09 am

    Great Post! You are sharing a wonderful post. Thanks and keep sharing.

  3. Henry Thomas says

    August 12, 2023 at 7:24 am

    This blog is helpful for those who are new to this trend. Cowboy boots are classical which makes your personality attractive. Try pairing these boots with Rip Wheeler clothing and see you will look more beautiful. Thanks for sharing this blog.

  4. Eli Richardson says

    October 2, 2023 at 10:53 am

    It’s awesome that your post talked about styling cowboy boots with different patterns. My oldest sister’s been focused on building her dream wardrobe for the past weeks, and she’d love to buy cowboy boots. I’m positive she’d love to read your intake on pairing simple cowboy boots with different textures to create an elevated look.

  5. Vanessa says

    February 28, 2025 at 5:48 am

    Thank you for this!! I have some beautiful boots that really stand out (subtle stiched butterfly pattern with reds, yellow, turquoise)…and reading that I need to let them shine and not worry about wearing plaid was all I needed to see! It was the perfect blog for me to find for today! (Go Texan Day).

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greta  / nashvillian / content creator / traveler / dog mom / breast cancer fighter

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