Just 15 Cute Dresses To Wear With Cowboy Boots

·4 min read

Saddle up, cowgirl, because cowboy boots are back and better than ever. In the past, I’d worn mine exclusively to country concerts and outdoor tailgates, but Gen Z has me convinced that they’re the shoe of the season, so catch me pairing them with absolutely everything. In particular, I’m gathering up the best dresses to wear with cowboy boots, from itty-bitty minis to flowy farm-chic maxis. One thing’s for sure—if you want to try the look, you’ve got options.

The art of styling cowboy boots isn’t as tricky as it seems, so long as you’re thinking about silhouette. While I love a good bodycon moment on the reg, a little frill and flare can be a fun contrast for heavy boots, so think about floatier A-line shapes that don’t necessarily cinch at the waist.

You might think you need to rock a mini with such tall boots, but I’m here to argue that midis and maxis look just as good. In fact, they allow for the element of surprise—a cheeky cowboy boot looks so cute peeking out from a voluminous skirt.

Still, I get that planning outfits around your statement boots can be tricky, so I’ve taken the liberty of making a shortlist of the bets dresses to wear with cowboy boots below, from brands like Selkie, Reformation, ASTR the Label and more.

Read on and prepare for compliments.

Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Target is a STYLECASTER sponsor, however, all products in this article were independently selected by our editors. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.

Courtesy of A New Day.
Courtesy of A New Day.

Sleeveless Dress in Pink

A floaty maxi that doesn’t look heavy is perfect for showing off a sneak-peak of your boots. This A New Day pick comes in eight shades in standard and plus sizing.



Sleeveless Dress in Pink $27.99


Buy Now

Courtesy of Eloquii.
Courtesy of Eloquii.

Eyelet Easy Dress

Eyelet cutouts feel so dreamy farmgirl to me—but make it fashion! I love the contrast of the high collar and long sleeves with the short hemline.



Eyelet Easy Dress $149.95


Buy Now

Courtesy of Majorelle.
Courtesy of Majorelle.

Sunbeams Dress

This is exactly the dress I want to wear with tan cowboy boots to flex on absolutely everyone during a night out. Can you blame me?



Sunbeams Dress $188


Buy Now

Courtesy of Eloquii.
Courtesy of Eloquii.

Smocked Front Mini Day Dress

A boxy dress with puff sleeves and a square neckline is the ideal sweet silhouette to rock with cowboy boots. This Eloquii one comes in four colors and sizes 14-28.



Smocked Front Mini Day Dress $119.95


Buy Now

Courtesy of Universal Thread.
Courtesy of Universal Thread.

Puff 3/4 Sleeve Tiered Dress

I’m a sucker for a white-dress-with-cowboy-boots combination, so this boho off-the-shoulder moment is a must-have for me, available in standard and plus sizes.



Puff 3/4 Sleeve Tiered Dress $29.99


Buy Now

Courtesy of Wild Fable.
Courtesy of Wild Fable.

Smocked Waist Fit & Flare Dress

This Wild Fable ruched floral mini is the perfect pop of color for your end-of-summer wardrobe. I love the orange, but there are four more colorways to choose from.



Smocked Waist Fit & Flare Dress $25


Buy Now

Courtesy of Reformation.
Courtesy of Reformation.

Crimini Dress

Reformation’s slip dresses reign supreme. Ones like this with a high slit allow you to show off your boots in a big way.



Crimini Dress $128


Buy Now

Courtesy of Selkie.
Courtesy of Selkie.

Selkie The Puff Dress

Yes, you can style your Selkie creampuff dresses with cowboy boots. The contrast is honestly perfection.



Selkie The Puff Dress $295


Buy Now

Courtesy of Never Fully Dressed.
Courtesy of Never Fully Dressed.

Postcard Wrap Dress

Never Fully Dressed wrap dresses can be tied up a few different ways, so you’ll have plenty of options for showing off your boots.



Postcard Wrap Dress $145


Buy Now

Courtesy of A New Day.
Courtesy of A New Day.

Sleeveless Dress in Light Brown

Remember that floaty maxi from Target I mentioned earlier? It also comes in this perfect neutral stripe for fall layering.



Sleeveless Dress in Light Brown $27.99


Buy Now

Courtesy of ASTR The Label.
Courtesy of ASTR The Label.

Saveria Off The Shoulder Tiered Midi Dress

Neutrals are definitely easiest for first-time cowboy boot stylers, so this tiered mocha midi would be a great option.



Saveria Off The Shoulder Tiered Midi… $148


Buy Now

Courtesy of Wild Fable.
Courtesy of Wild Fable.

Sleeveless Tiered Skater Dress

Something about the V-cut waist on this Wild Fable dress leans western to me, so it’s a perfect pick for pairing with your boldest boots.



Sleeveless Tiered Skater Dress $25


Buy Now

Courtesy of Reformation.
Courtesy of Reformation.

Brie Linen Dress

If flowy dresses aren’t your vibe, you can find a happy medium between those and full-on bodycon fits. This linen Reformation number is fitted, but still relaxed.



Brie Linen Dress $218


Buy Now

Courtesy of SKIMS.
Courtesy of SKIMS.

Ribbed Long Slipdress

HEAR ME OUT! This body-hugging SKIMS dress is a total wildcard, but it’s going viral on TikTok and would be perfect paired with boots for a fire Instagram ‘fit.



Ribbed Long Slipdress $78


Buy Now

Courtesy of ASTR The Label.
Courtesy of ASTR The Label.

Lorrie Sleeveless Ruched Midi Dress

I’m head over heels for this dress and its unique tie-front bodice. I favor the white, but it also comes in a sweet pastel lilac.



Lorrie Sleeveless Ruched Midi Dress $158


Buy Now

StyleCaster newsletter
StyleCaster newsletter

More from StyleCaster