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Just 11 Cute Dresses To Wear With Cowboy Boots

Stylecaster 6/2/2022 Bella Gerard

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 the 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 and Francesca’s are STYLECASTER sponsors, 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 Francesca’s. © Provided by StyleCaster Courtesy of Francesca’s.

Adrianna Gingham Mini Dress

Two of summer’s hottest trends combine to make this mini all the more stylish. The gingham puff-sleeved number is flirty and flowy—everything you could want for the warm months.

Courtesy of Target. © Provided by StyleCaster Courtesy of Target.

Flutter Button-Down Maxi Dress

A floaty maxi that doesn’t look heavy is perfect for showing off a sneak peek of your boots. This August Sky pick comes in ivory and mint colorways.

  a woman wearing a dress: Courtesy of Majorelle. © Provided by StyleCaster 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?

Courtesy of Reformation. © Provided by StyleCaster Courtesy of Reformation.

Marguerite Silk 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.

Courtesy of Selkie. © Provided by StyleCaster Courtesy of Selkie.

Selkie The Puff Dress

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

Courtesy of Target. © Provided by StyleCaster Courtesy of Target.

Wild Fable Triangle Cup Fit & Flare Dress

This cross-back fit and flare dress gives us major boho vibes, which always pair well with some boots.

Courtesy of Target. © Provided by StyleCaster Courtesy of Target.

Ruffle Sleeve A-Line Dress

You can’t go wrong with a ruffle-sleeved A-Line dress. This kind of effortless style looks good with any accessories and would pair so well with your favorite kind of boots.

Courtesy of J. Crew. © Provided by StyleCaster Courtesy of J. Crew.

Cotton Poplin Shift Dress

A shift dress with puff sleeves and a square neckline is the ideal sweet silhouette to rock with cowboy boots. This J. Crew one comes in a gorg floral pattern in sizes XXS to XXL.

a person wearing a dress: Courtesy of ASTR The Label. © Provided by StyleCaster Courtesy of ASTR The Label.

Saveria Off The Shoulder Tiered Midi Dress

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

a woman wearing a blue dress: Courtesy of Eloquii. © Provided by StyleCaster 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.

a person posing for the camera: Courtesy of SKIMS. © Provided by StyleCaster 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 perfectly paired with boots for a fire Instagram ‘fit.

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