Wear cowboy boots with dress

How to Wear Cowboy Boots with Dresses or Skirts?

How to Wear Cowboy Boots with Dresses or Skirts?

For hundreds of years, riding boots have been an integral part of horseriding attire, handcrafted in dozens of different styles by dozens of different regions around the world. The cowboy boot was influenced by the vaquero-style boot imported to the Americas from Spain in the 1600s and first appeared on the plains and deserts of the midwest and far west of the United States in the 1800s.

Cowboy Boots for Women

The cowboy boot is a tall boot that hugged the calf and was designed to keep the foot firmly fastened in the stirrups while riding. To avoid slipping, the angled heel sits securely in the bottom of the stirrup. Outside stitching has a practical purpose, preventing the leather from bending and preserving a strong shape around the leg rather than folding over.

For several years, since it was employed as military footwear for cavalry, the Wellington boot, one of the first mass-produced boot styles, was popular among cowboys in the United States for several years. Following the American Civil War, many former soldiers headed west to farm, herd cattle, and establish new towns, and the military boot fell out of favor, giving way to the traditional cowboy boot.

With the onset of industrialization, cowboy boots began to be produced in larger quantities with the onset of industrialization, as updated sewing machines and newer, better materials allowed for faster production.

Some of the most enduring cowboy boot companies can still be found in the American West, near where the first cowboy boots were created in Texas and Kansas.

Design Of The Cowboy Boot

The long shaft protected the legs from the bush, wetness, and other hazards while riding the horse, while the angled heel kept the boot tight in the stirrups without harming the rider by allowing the foot to become caught in the event of an accident.

Cowboy Boots

With the introduction of rodeos, a new type of cowboy boot, the roper, arose to meet the needs of riders. In the case of calf roping or other rodeo activities, the roper boot has a lower heel and shorter sides, allowing the rider to dismount and run.

The toe was either rounded or squared in the early days of the boot, making it more comfortable for the foot. As boots got more advanced in the 19th century, the toes were narrowed significantly to make it easier for the rider to insert his feet into the stirrups.

Cowboy boots did not begin to have an extremely narrow, styled pointy toe until the 1940s, during the fad of Western movies. This was the dominant style for numerous decades, despite the fact that it was less comfortable for the rider.

Best Dresses To Wear With Cowboy Boots

Cowboy boots are such an underappreciated fashion statement! In this post, we’ll teach you how to wear cowboy boots with the best dress for a modern Western aesthetic.

Cowboy boots are one of the most popular accessories to have in your collection when it comes to country fashion. Whether you’re dressing up for a night at the rodeo or just want some new boots to pair with your favorite denim, these are a must-have for any woman interested in Western fashion.

Cowboy boots are a must-have for every country girl’s wardrobe, but they can be difficult to dress up. If you’re getting ready for a night out with the gals or a date with your new crush, we’ve got some suggestions for what to wear. So, instead of wearing your favorite pair of cowboy boots with your favorite pair of skinny jeans, denim shorts, and crop top, pick out the right outfit to wear with your favorite pair of cowboy boots!

Cowboy boots are striking accessories that give your outfit a lovely Southern touch. Wearing a pair of cowboy boots with your favorite sundress is a lovely, fashion-forward combination that will turn heads everywhere you go, even if you don’t live in the South or the Midwest. And who knows, you could be the next big thing in your town or city.

Cowboy boots are now generally accepted in many cities, thanks to celebrities and models like Kendall Jenner, Miley Cyrus, and Dua Lipa, who have been spotted wearing them in public for the past few years. There’s no reason not to try on a pair of cowboy boots if you haven’t already!

This article will show you which outfits go well with cowboy boots and which ones don’t, so you can look your best wherever you go!

Bodycon Dress with Cowboy Boots

Who says bodycon dresses can’t be worn with cowgirl boots? Bodycon dresses aren’t commonly seen in Western clothing, but thanks to the ever-changing design business, this is a delightful contrast with a modern touch. This style of the dress hugs you in all the right places and accentuates your lovely curves.

You’ve got yourself a good bodycon moment if you pair it with some knee-high boots (cowboy style, of course). Wear a blazer to complete the ensemble for a trendy and beautiful appearance!


Choose a flowy, long dress if you want a flirtatious vibe. Because this dress is still classified as a “country dress,” it’s pretty simple to pair it with your favorite cowboy boots.

Mini Sundress with Cowboy Boots

First and foremost, if you already own a gorgeous tiny sundress, there’s no need to explore any further! Cowboy boots look great with sundresses, and the two look great together. Combine this dress with tan cowboy boots for a wonderful casual appearance that’s appropriate for any event!

Off-Shoulder Dress with Cowboy Boots

An off-the-shoulder dress is a must-have for your summer wardrobe! This look is ideal for a date night, a night out with the girls or even a sunny day at the ranch.

Plaid Dress with Cowboy Boots

Plaid (or gingham-patterned) western dresses are possibly the ideal garment to combine with a fantastic pair of cowboy boots. Flowy farm-chic maxis are the way to go if you’re striving for a whole Western appearance. Finish it off with a hat, and you’re ready to go!

Wrap Dress with Cowboy Boots

Wrap dresses, especially in the summer, are a terrific alternative to pair with Western boots. Flowy, airy, and available in a variety of styles, this summer favorite is a must-have.

How to Wear Ankle Cowboy Boots With Skirts?

When adding this versatile boot to our wardrobe, many of us wonder how to combine ankle boots with skirts. Because there are so many designs of skirts to pick from, it can be difficult to know which sort of ankle boots to pair with them to create beautiful outfits.

To assist you, here is a style guide for ankle boots with skirts (along with photos!) that will ensure you look put-together every time you wear this fashion combination.

Before we get into the finest ankle boots to pair with each style of skirt, let’s start with some basic fashion standards.

How to Wear Ankle Boots with Skirts?

The above is a good rule of thumb to follow when pairing your ankle boots with your skirts, to make sure your outfits are appropriately styled.

For a casual daytime look, chunky ankle boots in brown or black look great with above-the-knee skirts, such as denim, or jersey-material skater skirts.

When you want to look a bit more dressed up, wear heeled ankle boots with a shaft that fits your calf, with a more elegant style skirt. This style of ankle boot is a perfect option for the office if your workplace has a smart casual dress code. Match your boots with a pencil skirt or a knee-length skirt for a presentable and seamless style. Pair with tights in the cooler months to look even more put-together.

Denim Skirt with Cowboy Boots

Wear ankle cowboy boots with a light wash of indigo wash denim skirts and a crop top for a casual daytime look, or with a jumper and tights in the cooler months. For a more glamorous evening appearance, pair black heeled ankle boots with a black denim skirt and a lovely shirt.

To demonstrate how adaptable this pairing can be, I created three alternative outfits with my ankle cowboy boots and denim skirts.

Wear a mustard sweater with a basic denim skirt and ankle boots for a casual daytime look. A thick belt and a monochromatic bag complete the look.

Pair your denim skirt with ankle boots that have extra detail to liven it up. For a splash of metallic contrast, I designed ankle boots with a gold heel for the middle and right-hand outfits. To create dressier alternatives for this duo, I used red as the focus color for the outfits.

Long Skirt with Coyboy Boots

If you’re going to wear ankle boots with a long skirt, make sure they’re heeled and the hem of the skirt doesn’t pass through the shaft of the boot. Showing off your ankle boots rather than burying them in the fabric gives them a lot more attractive appearance.

Two more formal appearing shirts are coupled with elegant ankle heels for a sophisticated twist. Ankle cowboy boots are often thought of as a more casual shoe, but they may look amazing when paired with a dressier long skirt.

The easiest ankle boots to match this manner are black, heeled ankle boots with a tall shaft. For the warmer months, brown heeled ankle boots would look great with white, cream, and neutral-toned formal shirts.

Midi Skirt with Cowboy Boots

When wearing ankle cowboy boots with midi skirts, choose a sleek model with a height shaft and a calf-length shaft. Heeled ankle boots are preferable to flat ankle boots because they stretch the legs and highlight the skirt’s silhouette.

Ankle boots, like midi skirts, look fantastic with heeled shoes. There are so many different designs of ankle boots to choose from that finding a more exquisite pair to wear with your dressier skirts is a breeze.

For a more formal look, I teamed my black heeled ankle boots with three different midi skirts and tights in the image above.

Short Skirt with Cowboy Boots

Choose a lower-heeled boot for casual daytime short skirts and a heeled ankle cowboy boot for dressier nighttime short skirts when wearing ankle boots with short skirts. If you’re wearing a short skirt with tights, match the color of the boots to the tights. If not, coordinate the color scheme of your skirt to the boots.

Lighter-colored ankle boots are matched with lighter-toned and natural-toned short skirts in the top image to produce attractive color palette pairings that look wonderful in the summer.

For three put-together looks, black ankle boots are combined with black, denim, or neutral short skirts in the image below. The outfit on the left is appropriate for an evening out, the outfit on the middle is appropriate for a smart casual function, and the outfit on the right is appropriate for transitioning between seasons.

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Sphie Ross

Sophie Ross has written, edited, and produced beauty and fashion content for more than 3 years. She works full-time in the fashion and beauty categories as a copywriter, but she is passionate about all things related to beauty.