16 Dresses to Wear With Cowboy Boots in 2024

1

this breezy slip dress

H&M Pleated Camisole Dress

Pleated Camisole Dress

Go for a long, limeade-green dress with a pair of neon cowboy boots peeking out from underneath for a combo that's anything but traditional!

2

this Americana denim dress

The A&F Mara Denim Vest Mini Dress

Mara Denim Vest Mini Dress

There's nothing more classic than cowboy boots and denim! This little button-front dress would look 10/10 with a pair of brown leather boots and a hat.

3

this open-knit midi

H&M Ladder-Stitch-Look Knit Dress

Ladder-Stitch-Look Knit Dress

Pop a slip underneath (or not!) and wear this bad boy out to dinner all year long. For accessories, think sleek white boots and a matching bag.

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4

this unique drop-waist dress

Motel Payoda Bandeau Drop Waist Mini Dress

Motel Payoda Bandeau Drop Waist Mini Dress

Presenting the perfect summer barbecue/tailgate/game day dress! The drop waist silhouette has been trending hard, and who can say no to that gorgeous French blue print?!

5

this flirty corset dress

Fenity Charlotte Dress

Charlotte Dress

This little mini (inspired by the iconic Charlotte York of Sex and the City, obviously!) styled with some cowboy boots?! Take my money!

6

this breathable linen dress

The A&F Mara Squareneck Linen-Blend Vest Mini Dress

Mara Squareneck Linen-Blend Vest Mini Dress

This is a weekend brunch dress if I've ever seen one. Plus, cowboy boots can get a liiiiitle sticky around your legs in the summer so a breathable fabric like linen will balance things out!

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7

this romantic midi

Bardot Esra Midi Dress

Esra Midi Dress

Take this TikTok-viral corset silhouette (the kids are calling it a milkmaid dress, FYI) and add a little yeehaw spin to it with a pair of cowboy boots!

8

this beachy sundress

Lemlem Gigi Sundress

Gigi Sundress

This pink and orange sundress is sooo East Coast Summer—anyone else suddenly craving a lobster roll and an aperol spritz?

9

this blingy mini

Good American Smooth Matte Crystal Mini Dress

Smooth Matte Crystal Mini Dress

Hi Birthday Barbie! Sparkly cowboy boots will be wayyyy more comfortable (and way more on theme) than stilettos for a night of dancing.

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10

this whimsical postcard dress

Reformation Cami Linen Dress

Cami Linen Dress

Headed on a Euro getaway this summer? Don't forget to pack this funky little mini dress and a pair of matching sunnies!

11

this metallic silver dress

MORE TO COME Yarina Mini Dress

Yarina Mini Dress

They don't call it Disco Cowgirl for nothing—top off this glitzy silver mini with a pair of matching cowboy boots for a bachelorette or birthday party.

12

this soft blue sundress

ZESICA Floral Printed Strapless Maxi

Floral Printed Strapless Maxi

If you're headed to a semi-nice gathering (like a casual wedding or baby shower), you can't go wrong with a floral maxi dress. How cute is the ruched bodice?

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13

this easy denim romper

SheKiss Denim Romper

Denim Romper

Okay, so, not technically a dress, but this little denim romper was too good not to include. If you're hitting up a country music concert this year, a romper is the perfect throw-on-and-go item.

14

these metallic cowboy boots

Billini Homestead Wide Calf Boots

Homestead Wide Calf Boots

These cowboy boots are, if you'll excuse the obvious pun, totally out of this world. They'll look A+ with mini skirts or dresses.

15

these white(ish) cowboy books

Steve Madden Lasso White Denim

Lasso White Denim

These white denim boots are a little roughed up (see: the burnout detailing) for that authentic, I-wear-these-for-horseback-riding vibe. Plus, the pointed toe and stacked heel feels surprisingly elegant!

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16

these colorblocked boots

Dolce Vita Blanch Boots

Blanch Boots

Now 56% Off

Promise that you'll never get more compliments on a single piece of clothing as you will on these shoes. The unique contrast detailing makes 'em stand out from the rest!

Headshot of Hannah Oh

Hannah is the Shopping Editor at Cosmopolitan, covering all things from chic home decor to trendy fashion finds, TikTok products that are actually worth your $$$, and the perfect gift to buy for your boyfriend's mom. She previously wrote for Seventeen and CR Fashion Book. Follow her on Instagram for hot takes on red carpet fashion and pictures of her office outfits that nobody asked for. 

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