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8 Best Dresses to Wear with Cowboy Boots to a Fun Wedding

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Written by Kathi L.

Say “I Do” to these dresses that look great with cowboy boots for your next wedding guest appearance.

You have a horse-crazy friend getting married in a western wedding. It should be a blast!  You have the perfect gift and the perfect pair of cowboy boots ready. Except… the rest of your closet is full of jeans, breeches and coveralls. You need a cute country style dress that looks good with your boots.

We’ll look at what styles tend to look adorable with boots, including:

  • Short hems that come down to above the knee or mid-thigh
  • Dresses with a “handkerchief” hemline
  • V-shaped hemlines that are shorter on the sides and longer in the front and back
  • Slit-leg designs
  • High-low hemlines

Then, we’ll look at some specific dresses to see which styles appeal to you and align best with the type of western wedding you’re attending.

What Dresses Look Good with Boots

No matter what your style, you can find an outfit you love that looks super cute with boots and a hat.

  • Types of dresses that look good with boots typically include short hems that come down to above the knee or mid-thigh.
  • Dresses with a “handkerchief” hemline (i.e. uneven to look like a handkerchief) are solid choices, too.
  • V-shaped hemlines that are shorter on the sides and longer in the front and back can look good when paired with boots.
  • When you pair a longer dress with boots, those with a small slit on one leg are most fashionable as it allows you to show off at least one cowboy boot.
  • Dresses with high-low hemlines are also ideal for wearing with boots as they’re long but people can still see your boots.

Recommended Dresses

Dusty Turquoise Fields Dress

This dress brings class, beauty, and western flair. Perfect for wearing with your favorite western necklace. Here, I’ve paired it with a light tan colored pair of boots and stylish hat.

Click to see it on Amazon

What’s to Love:

  • Handkerchief hemline
  • Looks beautiful with boots
  • Sheer, lacy sleeves
  • A skirt that falls past the knee
  • Lovely turquoise color
  • Great for pear or inverted triangle body types

Read Customer Reviews on Amazon

Perfect Pairings: 

Andybridal Country High Low Wedding Guest Dress

Can you say versatile? This is a bridesmaid dress, but when it comes right down to it, you could wear this for a rustic wedding, a western wedding, or any other occasion.  The pairing possibilities are endless. Boots, a hat, a jacket, whatever your heart desires.

Click to see it at Amazon

What’s to Love:

  • Super cute style
  • Looks great with boots
  • Comes in tons of different color choices
  • Versatile and can be paired with many different hats and jackets
  • Chiffon fabric
  • Budget friendly
  • Flattering for inverted triangle and hourglass body types

Read Customer Reviews on Amazon

Perfect Pairings: 

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Missmay Women’s Vintage Floral Cocktail Dress

This is one of our favorite dresses. It’s affordable and has earned solid high ratings on Amazon. We love its elegant 50s-style look, as well.

Click to see it on Amazon

What’s to Love:

  • Drop-dead gorgeous lace dress
  • Would look super cute with boots and a hat
  • Lace, lace, lace!
  • Several flattering neckline styles to choose from
  • Comes in several different colors
  • Looks flattering on a variety of body types

Read Customer Reviews on Amazon

Perfect Pairings: 

Comfortable Cowboy Boots

One Shoulder Evening Chiffon Dress

This is another very versatile and stylish choice.  The lace gives this classy dress some western flair, and the partial slit in the long skirt allows you to show off those boots.

Click to see it on Amazon

What’s to Love:

  • Long and more formal
  • Comes in black also
  • Slit to show off your boots
  • Lace shoulder piece
  • Great for hourglass and rectangle body types

Read Customer Reviews on Amazon

Perfect Pairings: 

Chocolate Cowgirl Social Dress

This beauty comes with sheer lace sleeves and is the ideal color for pairing with brown boots and a hat. Adding a bit of blue into the mix can be fun, as shown with the model’s necklace.

Click to see it on Amazon

What’s to Love:

  • Chocolate Brown western dress
  • Perfect for apple and pear body types
  • Plus-size
  • Lacey, flowing sleeves
  • Short skirt
  • Western flair

Ready Customer Reviews on Amazon

Perfect Pairings: 

Mmondschien Women’s Wedding Formal Dress

This dress is an absolute showstopper.  It combines a classy black color with a sheer lace neckline for western flair.

Click to see it on Amazon

This dress also includes a slit that allows your boots to stand out.  I think combining this dress with the boots and hat below is the epitome of classy cowgirl.

What’s to Love:

  • Similar dresses that vary in color
  • Ultra-classy
  • Lace upper accents
  • Slit for showing off boots
  • Versatile black color

Read Customer Reviews on Amazon

Perfect Pairings: 

Boho Tassel Sundress

If you’re into more of a carefree, boho style, here’s a beautiful option. The colors are a bit limited (black or red), but this dress would look really cute with boots and a hat.

Click to see it on Amazon

What’s to Love:

  • Carefree, Boho vibe
  • Would look cute with a hat and boots
  • Ultra-cheap, but with good reviews
  • Versatile because it’s a sundress
  • Ultra-affordable
  • Would be great for an apple body type
  • Comes in many different colors

Read Customer Reviews on Amazon

Perfect Pairings: 

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Modecrush Women’s Ruffle Cocktail Dress

The high-low hemline dress is perfect for showing off your exquisite boots.

Click to see it on Amazon

What’s to Love:

  • V-neckline
  • Comes in eight different colors
  • Lace! I might be a fan of lace…
  • High- low hemline for boot visibility
  • A great A-line skirt for those inverted triangle types
  • Extremely affordable and has a ton of good reviews

Read Customer Reviews on Amazon

Perfect Pairings: 

Finding Your Style

  • If you’ve got an apple body type, tunic and shift dresses (dresses that fall straight down from the neckline to the hemline) are perfect, especially when combined with a short hemline.
  • If you have a pear body type, choose things that accentuate your upper body like prom style and fit and flare dresses (dresses with a fitting waistline and A-line skirt). Dresses with sleeves are also a good choice as they draw attention to the upper body.
  • If you’ve got an hourglass figure, go for dresses with belts in the middle (or add them yourself) to accentuate your curves.
  • If you have broad shoulders and small hips (an inverted triangle body type), try a ruffled or A-line hem to balance out your shoulders or a maxi dress to make your hips look more full.
  • If you’ve got a rectangle body type (straight up and down with undefined curves), you can pretty much wear any style. Dresses with belts or cinched middles help to give the illusion of curves.

Fashionably Ever After

We hope you’ve enjoyed scrolling through these cute dresses, and you can’t go wrong when you pair them with your boots, a cool hat, and wedding fun!

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About the author

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Kathi L.

When I'm not helping equestrian businesses market themselves online, you'll find me hanging out at my barn in Nebraska. I grew up riding in 4-H, have worked as a colt trainer and trail guide, and have even competed in Extreme Mustang Makeover Challenges. Now, I've found a new love for dressage and love taking lessons in this discipline!