6 Best Dresses to Wear with Cowgirl Boots [Style Guide]

Woman in front of old car at hamburger stand wearing a dress with boots and a hat

Wondering what dresses to wear with cowgirl boots? Discover today's trending looks and the best boots to pair with them.

Recently we chatted about the Best Jeans to Pair With Cowgirl Boots. But when the occasion calls for something more fun, formal, or summer heat-friendly, what’s a girl to do? Well, why not pair a trendy dress with cowgirl boots you’re crazy about?

Whether you need a fun and flirty ensemble, or something a little more formal, we’ve got the low-down on the best dresses to wear with cowgirl boots so you can head out in style to your next event.

The 6 Best Dresses to Wear with Cowgirl Boots

While there are certainly wrong ways to pair a dress with cowgirl boots, we’re happy to announce there are far more ways to get it right. Maybe it’s the boots talking, but it’s actually quite impressive how many dresses pair well with cowgirl boots, short and tall. 

For now, let’s stick with the positives and dig into the six best dresses to wear with cowgirl boots, all of which can be fashioned in mini, midi, and maxi dress styles with short or tall boots.

Western Dresses

Today’s most popular western dresses pay homage to their 19th-century ancestors but have spruced things up a bit in terms of look and fit. Instead of stiff bodices, full-length sleeves, and necklines so high and tight you could choke, today’s best western dresses are dripping in flattering fits, deep v-necklines, flowy fabrics, adorable sleeve styles, and mini, midi, and maxi-lengths for a perfect fit no matter your preferred style.

If you’re looking for one of the best dresses to wear with cowgirl boots, western dresses lead the charge. Below are two styles of western dresses to wear with boots like The Annie, our tall cowgirl boots in Sienna suede (left) and Midnight (right).

Women wearing dresses and cowgirl boots sitting on blue velvet sofa

Our tour of the wild west fashion options world doesn’t end there! Just look at how this traditional western-inspired white midi dress pairs with The Penny in Scotch goat, a simple look any cowgirl would fall head over heels for.

Woman in white dress holding pair of booties

Have a pair of white cowgirl boots you’re dying to hit the town in? Why not pair them with a western dress in a light and refreshing color or dainty print, like we did below with a pair of women's ostrich boots?

Woman leaning against column wearing a dress and white ostrich boots

Bohemian-Style Dresses

The bohemian or “boho chic” style is a tried-and-true staple that’s stood the test of time since the 70s. This style is characterized by bold yet relaxed looks in loose-fitting silhouettes that look darling with classic leather and flashy boots. Whether you’re after that Stevie Nicks style with leather and lace and captivating patterns or fancy yourself the simplicity of crisp white cotton, linen, sun-kissed neutrals, and mini, midi, and maxi-length looks, there’s no shortage of ensemble opportunities to pair with your favorite tall or short cowgirl boots.

Pro Tip: When pairing a flowy boho dress with any boot style, accentuate the look and your figure with a matching belt around the waist. This can help break up bold patterns and prevent a “frumpy” look.

Floral Dresses

Next on our list: floral dresses with cowboy boots. While many western dresses feature dainty floral designs, not all floral dresses are necessarily western. Floral dresses come in various colors and cuts that can move effortlessly through the seasons with you, and simple looks never go out of style. Here are a few looks we’re loving, starting with this gorgeous floral dress paired with The Penny in Sequoia bovine.

Woman in floral dress and booties riding a horse

Woman lifting up hem of her floral dress to showcase booties

Here’s another tried-and-true favorite look featuring The Josie boot in Sienna suede.

Woman crossing ankles wearing suede boots standing in a kitchenWoman in a field with wildflowers wearing suede boots

A classic look for spring, summer, and fall is a maxi dress with low-cut cowgirl boots, pictured below with The Daisy boot in Sienna suede.

Woman in suede booties sitting on the tailgate of an old pickup truck


Whether off-the-shoulder, strapless, halter, or spaghetti straps, sundresses are a crowd favorite for moving comfortably on hot summer days without sacrificing style. Just look at how The Penny boot in Sequoia bovine pairs with this yellow midi dress.

Woman wearing yellow sundress and brown booties

Woman wearing yellow sundress and brown booties

Smocked Dresses

Smocked dresses are designed using a special embroidery technique, where fabric is folded into an accordion or pleated style. The result is a flowy yet feminine silhouette that looks great with everything from sandals and sneakers to your favorite pair of boots. Smocked dresses come in every length, color, and style, making it simple to find your favorite look.

Formal Dresses

If you’ve ever attended a “country cocktail” style party or wedding, chances are you’ve seen this look—formal dresses and cowgirl boots. A delicate balance between casual and formal, this look is one best reserved for dedicated “country cocktail” inspired parties or events, and you can’t go wrong with a little black cocktail dress and a pair of gorgeous leather, suede, or exotic cowgirl boots with a fun and flirty dress to match! 

Just take these two looks below, which feature The Savannah Boots in Bone python.

Woman dancing in white boots and white cowgirl hatWoman in a pink dress and white hat wearing white cowgirl boots

Step into Style with Tecovas Women’s Boots

No matter which style dress fits you best, rest assured that Tecovas has a pair of hand-crafted cowgirl boots to make sure you stand out every time you step into the room. Browse and shop Tecovas today to find your must-have pair for every look you love to rock.

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