Outfits with Cowgirl Boots; Suave Ways to Wear Them.

cowgirl boots outfit

It wasn’t long ago when cowgirl boots were worn only as part of costumes. Today, cowgirl boots are one of the most fashionable shoes out there. The last time boots were this famous was when Hannah Montana was at an all-time high. 

The western style of clothing continues to be a huge part of fashion today. Duster coats, checked shirts and boots are a few well-known examples. Cowboys wore clothes and boots that would help them tackle the forces of nature. They chose clothes that would resist sand and would prove to be durable. The modern-day fashionista wears clothes, not for their occupational benefit but, instead for the sake of fashion.  

Western fashion revolved around a set color scheme. It included brown, black, beige, and blue. The splash of color came from different variations in checked shirts. Hats, belts, and boots were major accessories and, dare I say, carried the whole look.

It can be daunting to try and pair cowgirl boots with modern-day clothing but isn’t fashion all about taking risks? There is no right or wrong. It is up to you to figure out what works for you and what doesn’t. Firstly, it’s important to understand what a cowgirl boot is, what it looks like and what it pairs best with.

What are Cowgirl Boots?  

There are many different types of boots, like Chelsea boots and knee-high boots, but what sets cowgirl boots apart is their distinguished tall boot shaft. The heel of the boot is a characteristic angled sort and adds around an inch to your existing height. The boot comes up to mid-calf level and reflects beautiful craftsmanship. 

Types of Cowgirl Boots 

There are two main types of cowgirl boots. 

Classic – This style has a long boot shaft, an angled heel, and a narrow pointed toe.

Roper – This style has a shorter shaft with a low square or rounded toe. 

Outfits to Wear with Cowgirl Boots 

Cowgirl boots would look best with cowgirl outfits (obviously), but since we don’t live in the wild wild west, you need to learn what modern-day clothing items and styles would look best with these rustic boots. 

Down below are twelve different ways you can wear cowgirl boots and kill it!

Denim Darling 

Jeans are something you will find in every person’s wardrobe. Pair a denim shirt with faded blue denim jeans and a pair of brown cowboy boots. Make sure the jeans end somewhere near the calves so that your boots are the center of attention. 

Something about denim just adds to the whole cowboy aesthetic and not to mention it serves as a reminder of the durable clothing styles actual cowboys preferred. 

The boot-cut style of jeans is a popular choice to pair with boots of all sorts (for obvious reasons). They are figure-hugging and have just enough flare at the bottom hem to compliment the structure of the boots. Pair the jeans with a leather tube top for a playful look. 

Lady Lace 

A lacy black top paired with a floral mini skirt and black cowboy boots creates a party-appropriate outfit. The lacy top, color coordinates with the black leather boots, and the floral skirt adds a touch of flirtiness to the whole outfit. 

Alternatively, you can swap the mini skirt for a leather skirt to create a date night outfit. Add on gold accessories to complete the look.

Enviable Boots 

If you want your boots to stand out, it’s important to keep the rest of the outfit quite basic. Try pairing a white tank with an oversized cardigan. Throw on biker shorts that match the color palette. Pick the most eye-catching pair of cowgirl boots, with bold colors and eccentric designs. Add a purse to complete this out-of-the-ordinary look.

When Country Meets Casual 

Whether you are going to spend the day at the park,  have lunch with friends, or even just run errands, you can do so while looking fantastic. Keep things casual and pick a high-neck sweater. Tuck it into a pleated white skirt and complete the look with a pair of white cowboy boots. Add a colorful bag to add some life back into the outfit.

Westside with a Touch of Glamor 

Pairing a dress with cowgirl boots may seem unconventional but trust me it works. The trick is to match the tones of the dress with that of the boots. Pick a mid-length printed dress and pair it with complementary boots. When picking a dress, gravitate towards neutral and earthy tones for a better match with the boots. 

Cowgirl Streetwear 

Streetwear fashion is all the talk these days. It’s all about creating a captivating look. Bring cowboy fashion to the streets by pairing a plaid shirt with black leather leggings and dark brown cowgirl boots. The look is easy to create and makes a statement.

Leather but Cowboy Style 

A brown leather jacket when paired with a simple white tank and denim blue jeans create a modern depiction of western style. If you’re feeling brave, top the look off with a brown cowboy hat and strut in style.

Alternatively, you can wear a black leather tank-top with cargo pants and black cowboy boots. The overall look is mysterious, bold, and striking. 

Boho Chic 

If you want a bare minimum but chic look then try pairing an oversized shirt with shorts and a pair of leather boots. Style your hair with beachy waves and add a statement necklace to keep with the boho theme. 

Cowgirl Barbie 

Barbie will always be the ‘It Girl’ when it comes to fashion and rightly so. Try out an iconic Barbie look by pairing a bright pink mini dress with a white linen shirt or a leather jacket and brown cowgirl boots. Add a pair of sunnies and you have yourself a winner. 

Upper-Class Cowgirl 

High-class fashion is a bit more difficult to succeed in. The key to mastering it is learning how to layer and mix and match prints. To create a sophisticated Sabrina Van der Woodsen (from Gossip Girl) kind of look, try pairing a chic gray sweater with a mid-length beige skirt. Add a snake-print long coat and top the look off with silver cowgirl boots. Put on a headband and matching socks to seal the deal.

White Dress Brown Boots 

White and brown make a classic combination. Create the perfect evening party look by pairing a white lace mini dress with a pair of brown cowboy boots. You can also substitute the white mini dress with an  A-line dress( with puffy sleeves) instead for a more sophisticated cowgirl look. 

Feeling a Little Silky

Silk dresses look extremely elegant on their own but when you pair them with cowboy boots you get the best of both worlds. The result is a powerfully-glamorous outfit. Pair a silk wrap dress with dark brown cowboy boots. Add a statement clutch and you’re ready to take on the world.  


How to wear cowboy boots after 50?

You can pair a white button-down shirt with a pair of dark blue denim jeans. Add on brown cowboy boots to complete the look. Alternatively, you can wear a printed midi dress with matching boots and minimal accessories. 

How to wear short cowboy boots?

Short cowboy boots look especially cute with short dresses, skirts, and shorts. You can also pair them with black jeans for a more casual look.

Can you wear overalls and cowboy boots?

Yes, you can, but, only if you’re going for a ‘classic cowgirl look’. Overalls, when paired with cowboy boots, create an occupational outfit rather than a modern one. 

How to wear ankle cowboy boots?

Ankle cowboy boots look great with denim shorts, printed long dresses, matching two-piece outfits, mini-dresses, and jeans. ankle cowboy boots are a more wearable style as they don’t overshadow the rest of the outfit. 


Cowgirl boots are a statement piece. They are both rustic and feminine. Their earthy hues replicate the tones of the sands on which cowboys trotted on their horses. The delicate stitching and intricate craftsmanship make them a fashion favorite. They come in various colors and with distinct detailing ensuring that there is something for everyone. 

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