What To Wear With Cowboy Boots For A Chic Western Look

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If you’ve recently incorporated a pair of Western boots into your wardrobe, take a look at our top tips on what to wear with cowboy boots!

While Western wear has been around forever and a day, we’re currently seeing a new surge in the popularity of Southern fashion among everyday people, as both Nashville and Texas have become hotspots for tourists. If you’ve booked yourself a Southern getaway, you may be wondering how to incorporate one of the area’s most beloved accessories into your outfit – the cowboy boot.

The Best Nashville Outfits: Denim wrap shirt dress and cowboy boots

Get this dress on Show Me Your Mumu

Cowboy boots have remained popular for decades and seemingly float in and out of fashion weeks’ runways every few years. Recently, they have been dubbed (again) as one of the hottest trends by Vogue, with celebrities like Dua Lipa, Kendall Jenner and Em Rata sporting the look.

However, if you haven’t worn cowboy boots before, it can be challenging to figure out what to wear with them to give off an effortless vibe. Whether you’re looking to dress up or dress down, there are plenty of ways to style your cowboy boots and create a chic and fashionable look.

In this article, we’ll explore different outfit ideas and provide tips on how to pair cowboy boots with different types of clothing. Whether you’re a seasoned cowboy boot aficionado or new to the trend, you’re sure to find inspiration and ideas for how to wear this classic footwear in a fresh and modern way.

What To Wear With Cowboy Boots

1. Floral Dresses

What To Wear With Cowboy Boots: Cute floral dresses
Get this floral dress at Show Me Your Mumu
What To Wear With Cowboy Boots: Black floral mini dress with long sleeves
Get this dress on Pink Lily

Wearing cowboy boots with a floral dress is a fun and stylish way to add a bit of Western flair to your outfit. To pull off this look, choose a pair of boots that complement the colors in your dress – we love light neutral cowboy boots the most.

When it comes to the length of your dress, shorter dresses that finish above the knee are usually the best, so you can show off your boots in style. Finally, accessorize your outfit with a cowboy hat, a statement belt, or even a denim jacket if it’s cooler outside.

2. Western Rompers & Jumpsuits

Cute black denim dress with black cowboy boots
Get this denim romper at Show Me Your Mumu
What To Wear With Cowboy Boots: Brown floral shirt dress
Get this romper at Show Me Your Mumu

Cowboy boots can add a touch of rugged charm to a Western-inspired denim romper, making for a stylish and playful outfit.

Rompers are a great alternative to dresses if you’re concerned about practicality. For example, if you felt the sudden urge to want to go on an impromptu horseback riding session on your Southern getaway, it’s much easier to do so in a romper rather than a dress.

3. Blazers

If you’r a city girl and looking to incorporate cowboy boots into your everyday attire, blazers are an easy way to make your outfit work. They can be thrown on top of multiple different looks, including everything from a feminine maxi dress, all the way to a more casual outfit with jeans or shorts.

If you’re looking for the perfect balance between a Western and modern look, this combo should be on your radar this season.

4. Jeans

Cowboy boots and jeans are a classic combo that has been around as long as the boots have existed. Nowadays, you can wear cowboy boots with almost any type of jeans, ranging from skinny, to slightly baggy, to bootcut, to wide-leg jeans.

If you’re wearing straight-leg or skinny jeans, tuck them into the boots to show off their shape and elongate your legs. For bootcut or flared jeans, let them drape over the top of the boots to create a seamless look.

Alternatively, if you’re going for a more casual or relaxed look, try pairing your cowboy boots with a pair of distressed or rolled-up jeans. There are so many options – just choose a style that you normally gravitate towards!

5. Sweater Vests & Sweaters

Sweater vests and chunky knits have become a fall staple – they’re versatile, and stylish and can be worn on top of almost anything.

Wear your sweater vest with an oversized button-down shirt for a dress-like effect, and pair it with cowboy boots in a matching hue, like in the outfit featured above. You can also pair your sweater vest with a cute little tennis skirt for an even preppier vibe, or simply wear a pair of denim jeans underneath for extra comfort.

Alternatively, simply opt for your favorite chunky knit and pair it with skinny jeans or a bodycon dress, as featured above.

6. Shorts

Cowboy boots and daisy dukes are another classic combo that you’ll often hear in country songs. However, you don’t need to wear shorts quite as tight and short as daisy dukes to rock this look – you can even opt for a sleek pair of tailored shorts with a blazer if that’s more your style.

7. Jacket / coat

While you don’t often need a coat in Texas or other Southern states, if you’re planning to wear your cowboy boots up North in the winter, you’ll definitely need one. Opt for a fringed jacket for a fully Western look, or instead, go for your regular neutral trench coat that looks good with everything.

8. Bodycon Dresses

While bodycon dresses may usually be reserved for a night out look, you can dress yours down by adding a casual shirt over it, like in the outfit featured above. Finish this look with a pair of Western boots for a festival-ready outfit that looks chic and relaxed at the same time!

9. Denim Dress

Denim dress with beige cowboy boots
Get this denim dress at Show Me Your Mumu
What To Wear With Cowboy Boots: Denim chambray babydoll dress
Get this dress on Lane201

Like cowboy boots, denim dresses are clothing pieces that immediately make you think of Western wear. So, it’s no surprise that these two go together so well!

For a more polished look, consider adding a belt to cinch in the waist of the dress and complete the ensemble. Finally, don’t forget to accessorize with a hat or jewelry to elevate your outfit and showcase your personal style.


Cowboy boots are a versatile and stylish footwear choice that can add a Western vibe to any outfit. Whether you’re going for a casual or dressy look, cowboy boots can add a touch of Southern charm and personality to your style.

From pairing them with jeans and a t-shirt to dressing them up with a floral dress, there are endless possibilities for incorporating cowboy boots into your wardrobe. Just remember to consider the color, style, and length of your outfit when choosing which pair of boots to wear.

By following these tips and experimenting with different combinations, you’ll be able to create outfits that showcase your unique style and personality. So, embrace your inner cowgirl or cowboy and add a pair of cowboy boots to your shoe collection today!

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