Cowgirl boots and leggings are two wardrobe staples that can seem tricky to style together. However, with the right pairings, you can make this combo work for both fashionable and comfortable looks. If you’re short on time, here’s a quick answer to your question: Match fitted leggings with cowboy boots that hit mid-calf for a flattering silhouette.

Stick to neutral colors on bottom and add interest up top with graphic tees, plaid shirts or feminine blouses.

In this detailed guide, we’ll cover how to wear cowgirl boots with leggings for different occasions, provide styling tips, give advice on boot and legging lengths, recommend top pairings, and more. Read on to learn how to rock this western look in 2023!

Factors to Consider When Pairing Cowgirl Boots with Leggings

Occasion and Setting

When it comes to wearing cowgirl boots with leggings, it’s important to consider the occasion and setting. Cowgirl boots can be a versatile footwear option, suitable for both casual and more formal events. For a casual daytime look, pair your cowgirl boots with leggings and a cozy oversized sweater.

If you’re heading out for a night on the town, dress up your cowgirl boots with a stylish tunic or dress and accessorize with statement jewelry. Whatever the occasion, make sure the overall outfit is appropriate and reflects your personal style.

Boot Height and Style

The height and style of your cowgirl boots can greatly influence the overall look when paired with leggings. Ankle or mid-calf cowgirl boots tend to work best with leggings, as they create a balanced and streamlined silhouette.

The intricate details and embellishments on the boots can also add a touch of western flair to your outfit. Whether you prefer a classic leather boot or a more modern suede style, choose a pair that complements your leggings and enhances your overall look.

Leggings Color, Fit, and Length

When choosing leggings to wear with your cowgirl boots, consider the color, fit, and length. Opt for leggings in neutral colors such as black, brown, or gray, as these will easily complement the colors and patterns of your boots.

Ensure that the leggings fit well and provide enough stretch for comfort. As for length, ankle-length or full-length leggings are the most flattering options when paired with cowgirl boots. However, if you’re feeling more adventurous, you can also experiment with cropped leggings or even patterned ones for a unique look.

Top Styles and Accessories

The top you choose to wear with your cowgirl boots and leggings can greatly enhance the overall outfit. For a casual look, a simple t-shirt or button-down blouse can work well. If you’re going for a more polished look, opt for a tailored blazer or a flowy bohemian top. Don’t forget to accessorize!

Add a stylish belt to cinch in your waist or layer on some statement necklaces for a touch of glamour. Remember, the key is to have fun with your outfit and let your personal style shine through.

For more inspiration and ideas on how to wear cowgirl boots with leggings, check out Country Outfitter or Western Boot Sales. These websites offer a wealth of information and tips on styling cowgirl boots for different occasions and settings.

Styling Tips for Different Occasions

Casual Daytime Looks

When it comes to casual daytime looks, cowgirl boots with leggings can add a touch of Western charm to your outfit. To achieve a laid-back and effortless style, opt for a pair of ankle-length leggings in a neutral color such as black or brown.

Pair them with a loose-fitting tunic or oversized sweater for a comfortable and casual look. Complete the ensemble with a pair of cowgirl boots that complement the color palette of your outfit. Whether you choose classic brown leather boots or a more adventurous embroidered design, the combination of leggings and cowgirl boots is sure to turn heads.

Date Night Outfits

For a romantic night out, cowgirl boots and leggings can be a surprising and stylish choice. To create a chic and feminine look, start with a pair of leather leggings that fit snugly and accentuate your curves. Pair them with a flowing blouse or a fitted top for a balanced silhouette.

To add a touch of Western flair, slip on a pair of sleek and elegant cowgirl boots in a bold color like red or turquoise. This unexpected combination will make you stand out from the crowd and show off your unique sense of style.

Work and Business Casual Attire

Wearing cowgirl boots with leggings to the office may seem unconventional, but with the right styling, it can create a sophisticated and professional look. Opt for a pair of high-quality leggings in a dark color, such as navy or charcoal gray.

Pair them with a tailored blazer and a crisp button-down shirt for a polished and put-together ensemble. To add a touch of personality, choose a pair of cowgirl boots with subtle embellishments or a sleek and sophisticated design.

Remember to keep the rest of your accessories minimal and let your boots take center stage.

When it comes to styling cowgirl boots with leggings, the key is to balance the Western aesthetic with the occasion and overall outfit. Experiment with different colors, patterns, and materials to create looks that are uniquely yours.

Whether you’re going for a casual daytime look, a romantic date night outfit, or a professional work ensemble, cowgirl boots and leggings can add a touch of flair and personality to any outfit.

Choosing the Right Boot Height

When it comes to wearing cowgirl boots with leggings, choosing the right boot height is essential to create the perfect look. The height of the boot can greatly impact the overall style and feel of your outfit. Here are three popular options to consider:

Ankle Cowgirl Boots

Ankle cowgirl boots are a versatile choice that can be paired with leggings for a chic and casual look. These boots typically reach just above the ankle, providing a comfortable and stylish option. They are great for those looking for a more low-key and subtle cowgirl vibe.

Pairing ankle cowgirl boots with leggings creates a balanced and streamlined look that is perfect for everyday wear.

Mid-Calf Cowgirl Boots

If you’re looking to add a touch of Western charm to your leggings outfit, mid-calf cowgirl boots are a fantastic option. These boots reach the middle of the calf and offer a bit more coverage and height compared to ankle boots.

They provide a classic cowgirl look while still being practical and comfortable. Pairing mid-calf cowgirl boots with leggings can create a stylish and slightly more dressed-up ensemble.

Knee-High Cowgirl Boots

For those who want to make a bold and statement-making entrance, knee-high cowgirl boots are the way to go. These boots extend all the way up to the knee and exude a strong cowgirl vibe. Pairing knee-high cowgirl boots with leggings can create a striking and eye-catching look that is sure to turn heads.

This combination is perfect for special occasions or when you want to make a fashion statement.

When choosing the right boot height, consider your personal style, the occasion, and the overall look you want to achieve. Remember, there is no right or wrong choice – it’s all about finding what makes you feel confident and comfortable.

Leggings Length, Color and Fit Considerations

When it comes to wearing cowgirl boots with leggings, there are a few important considerations to keep in mind. One of the first things to think about is the length of your leggings. The length you choose can greatly impact the overall look and feel of your outfit.

Leggings Length – Cropped, Ankle, or Full

There are three main lengths to choose from when it comes to leggings: cropped, ankle, or full. Cropped leggings typically hit just below the knee and can create a fun and casual look when paired with cowgirl boots.

Ankle-length leggings are a popular choice as they provide a sleek and streamlined appearance. Full-length leggings, on the other hand, offer maximum coverage and can be a great option for cooler weather or if you prefer a more modest look.

Neutral vs. Bold Leggings Colors

The color of your leggings is another important consideration. Neutral colors such as black, gray, or brown can create a classic and versatile look that pairs well with any style of cowgirl boots. On the other hand, bold and vibrant colors can add a pop of personality to your outfit and make a bold fashion statement.

It’s important to choose a color that complements your boots and personal style.

Fitted vs. Loose Leggings

When it comes to the fit of your leggings, you have the option of choosing between fitted or loose styles. Fitted leggings hug your curves and provide a sleek and streamlined look. They can be a great option if you want to show off the shape of your legs.

On the other hand, loose leggings offer a more relaxed and comfortable fit. They can be a great choice if you prefer a more casual and laid-back look.

When selecting the right leggings to wear with your cowgirl boots, it’s important to consider the length, color, and fit that best suits your personal style and the occasion. Experiment with different combinations to find the perfect look that makes you feel confident and fabulous.

Top Styles to Pair with Cowgirl Boots and Leggings

Graphic Tees and Tanks

One of the easiest and most popular ways to style cowgirl boots with leggings is by pairing them with graphic tees and tanks. This casual and effortless combination is perfect for a day out with friends or running errands.

Choose a tee or tank with a fun western-inspired graphic or slogan to add a touch of cowgirl flair to your outfit. Don’t forget to add some accessories like a statement belt or a cowboy hat to complete the look.

Blouses and Button-Downs

If you’re looking for a more polished and put-together look, consider pairing your cowgirl boots with blouses and button-downs. This combination is great for a casual office setting or a lunch date. Opt for flowy and feminine tops in solid colors or subtle patterns.

You can tuck the blouse or button-down into your leggings for a more tailored look or leave it untucked for a relaxed vibe. Either way, you’ll be sure to turn heads with this stylish pairing.

Flannels, Plaid Shirts and Denim Jackets

For a classic cowgirl look, nothing beats the combination of cowgirl boots, leggings, and flannels, plaid shirts, or denim jackets. This timeless ensemble is perfect for fall or winter and adds a touch of rustic charm to any outfit.

Layer a flannel or plaid shirt over a simple tee or tank and pair it with your favorite leggings and cowgirl boots. To stay warm, add a denim jacket on top. This look is effortlessly cool and will make you feel like a modern-day cowgirl.

Sweaters and Cardigans

When the weather gets chilly, there’s no better way to stay cozy and stylish than by pairing your cowgirl boots with sweaters or cardigans. Opt for chunky knit sweaters or oversized cardigans for a relaxed and comfortable look.

You can choose neutral colors for a more versatile outfit or go for bold and vibrant hues to make a statement. Layer your sweater or cardigan over your leggings and finish off the look with your favorite pair of cowgirl boots. You’ll be ready to take on the colder months in style.

Dresses and Rompers

For a feminine and trendy look, consider pairing your cowgirl boots with dresses or rompers. This unexpected combination adds a touch of bohemian flair to your outfit and is perfect for a date night or a music festival. Choose flowy maxi dresses or cute rompers in floral prints or solid colors.

The contrast between the delicate dress or romper and the rugged cowgirl boots creates a unique and eye-catching look. Don’t forget to accessorize with a statement belt or some delicate jewelry to complete the ensemble.

Remember, when pairing cowgirl boots with leggings, it’s all about finding the right balance between casual and stylish. Experiment with different combinations and have fun creating your own unique cowgirl-inspired looks!

Accessories to Complete the Look

When it comes to wearing cowgirl boots with leggings, the right accessories can take your outfit to the next level. They add a touch of personality and style, making your ensemble truly stand out. Here are some must-have accessories that will perfectly complement your cowgirl boots and leggings:


Belts are not only functional but also a fashionable accessory that can enhance the look of your cowgirl boots and leggings. A wide leather belt with a decorative buckle can add a Western flair to your outfit. Opt for a belt in a contrasting color to create a visually appealing statement piece.

Remember, belts are not just for holding up your pants; they can also be worn at the waist to cinch in your silhouette and create a flattering hourglass shape.


No cowgirl look is complete without a hat. A wide-brimmed cowboy hat not only protects you from the sun but also adds a touch of authenticity to your ensemble. Choose a hat that complements the color and style of your cowgirl boots.

Whether you go for a traditional straw hat or a felt hat with a decorative band, it will undoubtedly elevate your outfit and give you that Western charm.

Scarves and Bandanas

Scarves and bandanas are versatile accessories that can be worn in a variety of ways to amp up your cowgirl boots and leggings. Tie a colorful silk scarf around your neck for a pop of color or wear it as a headband for a boho vibe.

A bandana tied around your neck or wrist adds a playful touch and can be a nod to the Western heritage. Experiment with different patterns and prints to find the perfect accessory to complement your outfit.


Jewelry is the finishing touch that adds sparkle and glamour to any outfit. When wearing cowgirl boots with leggings, opt for jewelry pieces that reflect the Western theme. Layered necklaces with turquoise or silver pendants, statement earrings with intricate detailing, and chunky bracelets with Western-inspired motifs can all enhance your cowgirl look.

Don’t be afraid to mix and match different pieces to create a unique and personal style.

Remember, the key to accessorizing is to have fun and experiment with different pieces until you find the perfect combination that expresses your individuality and complements your cowgirl boots and leggings. So, go ahead and add some flair to your outfit with these accessories!


Cowgirl boots and leggings can make for a stylish combo when paired properly. Focus on choosing boot heights, legging lengths, colors and fits that balance each other. Add interest up top with graphic tees, feminine blouses, flannels and sweaters.

Pull the look together with accessorizes like belts, hats and jewelry. With these tips in mind, you can comfortably wear leggings with cowboy boots for casual daytime activities, dates, work and more. Have fun putting your own spin on this western-inspired look!

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