33 Best Dresses to Wear With Cowboy Boots

Whether you’re a country girl who lives for Stagecoach Festival, rodeos, and country music concerts or just a gal who loves the look of cowboy boots, we see you.

Cowboy boots are having their moment and I am here for it! And these warmer months means shorter hems, and a chance to showcase a great pair of cowboy boots.

Cowboy boots are incredibly versatile. You can wear them with skinny jeans in the cooler months, denim shorts during the warmer months or dresses all year long.

My go-to look when styling my favorite pair of cowboy boots is finding a fabulous dress to accompany it. Depending on your choice of dress, you can easily style boots down, for an everyday look, or up, for a night out or a wedding.

My styling choices tend to depend on my mood, but I have been relentlessly searching for all the best dresses to go with my cowboy boots. If you’re looking a cute dress to wear with a great pair of boots, look no further! Here’s some a ton of different types of dresses to wear the next time you want to rock a pair of cowboy boots!

Best Dresses to Wear With Cowboy Boots

Best Dresses to Wear With Cowboy Boots

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Let’s go girls.

1. Little Black Dresses

There is nothing more iconic than a little black dress. The little black dress is a great option for any event. Go for a night out, hit the farmer’s market, or head to a cook-out in this dress.

Pairing your little black dress with cowboy boots brings an All-American look to a timeless classic.

Side Ruched Embossed Bodycon Mini Dress in Black

A simple black dress with flattering ruching on the side. The square neck line gives it an added flair!

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Faux Wrap Dress

If you love the look of a wrap dress without it actually being a real wrap, this is the perfect dress for you! The ruching creates a flattering fit and the skinny straps make it perfect for date night!

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Endlessly Endearing Black Dress

Endlessly Endearing Black Dress

This chic little black dress has scalloped detailing along the neckline making it simple yet stunning!

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V-Neck and Bell Sleeve Shift Dress

This is a dress that I personally own! It’s comfy yet stunning and looks amazing with cowboy boots. Try a pair of tan cowboy boots and gold jewelry for a stunning look!

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v-neck black dress

2. Floral Dresses

Florals are a summer staple. They come around every year, yet every time I cannot get enough of them. True to say that my love affair with florals only gets stronger once we add in the right pair of boots.

A floral dress and a pair of cowboy boots adds a sweet touch, making this look irresistible.

Floral tie knot dress

Tie-Knot Floral Chiffon Mini Dress

You’ll be the star of any event you go to in this dress! It’s a mini length with a self tie bowknot at the front. The ruffle hem gives it an even more feminine vibe and the shirred waist gives it a flattering fit.

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Navy Floral Dress

If you’re looking for a bit more casual dress, this is a beautiful option! This dress comes in a variety of colors and bonus – there’s pockets!

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navy floral dress

vneck red floral dress

Plunge Neck Knot Front Dress

Shorter dresses look perfect with boots and this boho floral dress is a stunning option! It has an elastic waist, tie front and also comes in a variety of different colors.

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3. Off-the-Shoulder Dresses

The off-the-shoulder neckline is the kind of dress that screams elegance to me, which is why I tend to love an off-the-shoulder look.

Adding a pair of cowboy boots brings a fun element to any off-the-shoulder dress. It gives and easy-going, summer vibe.

Pleated Maxi Off-Shoulder Dress

This pleated maxi dress is one that will make a statement even without your cowboy boots! It’s flattering and comes in multiple colors.

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A-Line Off-the-Shoulder Dress

Want to show off your shoulders AND your boots? Look no further than this stunning dress! It has a beautiful tie in the back along with lantern sleeves and a ruffle hem. Come in many different colors.

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4. Bright Colored Dresses

When spring and summer arrive I am always ready to bring on the color. Bringing in bright colors to my wardrobe seems to often bring confidence into my life.

Add a pair of cowboy boots, and you have a show-stopping combo!

Patchwork Of My Dreams Mini

Patchwork of My Dreams

This stunning feminine mini dress has a patchwork-inspired design with lace and stripes throughout the dress. It comes in other colors too!

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Sunflower Dress

This casual cute dress is one that I also own (but in red!). It’s incredibly comfortable, has pockets and has an elastic back for a flattering fit. The buttons are fake so no need to worry about one coming undone while you’re on a date!

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sunflower dress

5. Special Occasion/Wedding Guest Dresses

As a Midwestern gal, not only do I wear cowboy boots for special occasions, I encourage it! It is so easy to dress up a pair of cute cowboy boots and keep you look elegant and formal.

Plus, you tend be be comfier for a night on the dance floor. If you’re heading to a western wedding or another special occasion, try out one of these beautiful dresses!

High Low A-Line Cocktail Dress

This beautiful dress shows off your cowboy boots with it’s high-low hemline! It comes in a ton of different colors so no matter the color of boots you have, you’ll be sure to find a dress that goes with it.

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Foley Curved Waist Party Dress

A metallic dress paired with cowboy boots is an unexpected yet stunning combination! This beautiful dress will show off your boots for any special occasion you have!

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Foley Curved Waist Party Dress

6. Maxi Dresses

Maxi dresses and cowboy boots make the perfect casual look. A long dress and boots make the perfect outfit for a farmer’s market and brunch or a date night on a cool summer night!

When fall arrives, just add a denim jacket for a casual look or a leather jacket for an edgy one!

rust maxi dress

Rust Maxi Dress

Another dress I own and love is this maxi dress! It comes in a variety of colors for any occasion. There’s a tie back making it a great fit whether you large or small chested and fits oversized.

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Tiered Maxi Tent Dress

I own this dress and LOVE it. It’s so comfortable, so versatile and incredibly comfortable. It comes in a variety of colors and bonus – it has pockets!

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tiered maxi dress

7. Midi Dresses

You can never go wrong with a midi cut dress. Let’s be honest, the midi dress is the perfect dress to wear with any cowboy boots. The cut of the midi dress showcases your boot, unlike a dress-focused maxi cut and leg-focused mini cut.

The Drop Midi Slip Dress

You can’t go wrong with a slip dress! Throw on your cowboy boots and you’re ready to go!

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Daily Ritual Midi Dress

If you want something more casual, this tiered midi dress is a great option! It’s colorful and whimsical and when paired with cowboy boots, it makes the perfect summer dress!

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8. Mini Dresses

Since I live in a place with harsh winters, I soak in as much sun as I can when it is out. That is why I opt for a mini dress when the sun and the heat arrive.

A mini dress doesn’t always have to be for a night out, but it is a fun, flirty way to wear your cowboy boots.

Floral Mini Dress

A fun, flirty dress with puff sleeves paired with cowboy boots? Yes please! This fun dress is so cute and would look great with boots!

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Mini Sundress

A simple sundress with pockets will be your go to dress for summer! It has adjustable straps to ensure a proper fit.

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9. Flowy Dresses

Do you ever want to look like you are floating into a room? Elegant and feminine, a flowy dress bring an ethereal feel to a summer look. Balancing the femininity with the cowboy boots is a look for the bold, but it never gets old.

Button Down A Line Dress

This beautiful flowy dress is a lovely option for a dressier occasion such as a bridal shower or church! The button are functioning buttons and this dress comes in a bunch of colors.

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Elia Long Dress

Want a dress that sways this way and that? This is your dress! It’s made of lightweight fabric with tiered seams. You’ll feel like a princess!

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10. Wrap Dresses

A classic silhouette, the wrap dress is a must have for your closet. Add a pair of boots and it just may be your new favorite outfit.

A wrap dress and your cowboy boots make the perfect country outfit.

Maxi Wrap Dress

The options are endless when it comes to this dress! It comes in so many different colors and shades, I’m certain you’ll find one you love!

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Zelda Wrap Dress

I’m not sure you can find a more perfect wrap dress to wear with cowboy boots! This denim dress is chic, stylish and perfect for just about any occasion!

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11. Boho Dresses

Summer is fun and free, and that is what the boho style encompasses. Adding a boho flair is easily one of my favorite twists on western wear. A beautiful boho dress and cowboy boots are the perfect pair.

white boho dress

Boho Floral Lace Dress

I have named this the perfect family photo dress! I own this dress in white and love it! It’s incredibly flattering and looks great layered with a denim jacket.

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Casual Floral Print Boho Dress

If you’re looking for something a bit more casual that shows off your boots, this is the way to go! This dress has a flowy hem and comes in a variety of colors.

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boho floral dress

12. Shirt/Skirt Sets

Matching sets are currently in, and I hope they do not go out of style anytime soon, because I am in love. Sets are easy to style, and the right set will style well with any cowboy boot.

The best part about a set is they can be styled separately, which makes your closet go farther.

green set

Two Piece Floral Outfit

This crop top and midi skirt set is a stunning option for a two piece set! It’s modest yet trendy all in one. Comes in lots of colors!

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Saylor Saskia Set

This beautiful set can be worn casual or dressy, depending on the boots and the accessories! It has a floral eyelet trim and wide stunning straps.

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saylor set

13. Boxy Dresses

When it is a hot day and you want that classic, babydoll look, you need a boxy dress. Sometimes you need a little room to breathe in the summer sun, and the boxy dress does that while looking adorable.

Paired with cowboy boots, the boxy dress feels country in all the right ways.

T-Shirt Dress

This flowy, boxy t-shirt dress is a great option for a casual brunch or outdoor concert! Comes in a variety of prints and colors.

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Flowy Mini Dress

This fun chiffon dress has a dot pattern to it! Like many of the others, it comes in plenty of other colors and has pockets!

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flowy mini dress

14. Western Dresses

With our country music playing on the radio, sometimes, you just need a classic, western style. You have the boots, now time for country dresses that bring us back to our sweetheart, country roots.

These dresses make me excited to head to a country music concert and a family event.

Long Sleeve Tie Waist Dress

Long Sleeve Tie Waist Dress

A long sleeve dress that’s floral print is a stunning option for a western dress! It has a dainty tie waist and a ruffled skirt to complete the look.

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Ruffle Layer Backless Dress

This mini dress is a feminine option for a western dress! It has a deep v in the front and is backless. Comes in lots of colors!

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country dress

15. Denim/Chambray Dresses

Another classic country look, the denim or chambray look will always be a favorite. A denim dress and a pair of cowboy boots is the look of an All-American girl. I would already like to call dibs on this look for Fourth of July.

long sleeve denim dress

Long Sleeve Denim Dress

This tunic style dress would look amazing with cowboy boots! Wear this to your local rodeo or out to brunch, either way you’ll be incredibly stylish!

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Tiered Chambray Dress

A classy chambray dress, this tiered popover shirtdress would look stunning with cowboy boots! Comes in 3 different shades.

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tiered chambray dress

Ditch the heels and bring out the cowgirl boots. Not only are they comfier, but the outfit options are also endless.

A good pair of cowboy boots can styled up or down, and will bring an element of fun to all of your looks. May we all channel our inner cowgirl and rock our cowboy boots this summer.

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  • Jen Biswas

    Jen has styled women for photo shoots, fashion shows, board meetings, work trips and most importantly, every day life! She's been hired to style many homes as well. Her aesthetic aims to make style approachable and practical, and most of all fun! She's a mom of 3 who loves frozen cookie dough, plants and a generous pour of creamer in her coffee. Her biggest joy is helping others find joy in personal style through practical tips and inspiration. She loves to share all of her styling secrets on Paisley & Sparrow! Feel free to send Jen a message or join the fun on Instagram!

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