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The Best Dresses to Wear with Cowboy Boots

Kick up your heels in a fabulous dress with some chic cowboy boots. Here are our top options.
the Best Dresses to Wear with Cowboy Boots

Dresses are a wonderful way to enhance your wardrobe and get away from the boredom that the same shorts and shirt combinations bring. They allow us to dress up a bit without being too formal and feel delightfully feminine in the process. The varying fabrics, dress lengths, colors, and patterns open up a world of wardrobe opportunities. With spring in full bloom and summer just around the corner, putting on a lovely flowing dress with a pair of boots is the perfect outfit for lunch with friends or a visit to the local farmer’s market.

If you want to add a little bit extra to your outfit, don’t shy away from mixing up your accessory selections. For example, you can elevate your look with some flashy jewelry or a chic hat. Or, you can take your look in a completely different direction by changing up your footwear, especially with a pair of cowboy boots. Here are some beautiful dress options that really caught our eye, so you can look your best when you’re out and about this spring.

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Knee-Length Knockouts

When you’ve found your favorite pair of cowboy boots, it’s hard not to want to wear them with everything. Maxi dresses are the perfect option to pair with tall boots, and for cool evenings, you can add a denim jacket or a cardigan. If you’ve got a favorite mini dress or little black dress, you can elevate your look by pairing it with some high cowgirl boots for a date night with your main squeeze or a night out with your girlfriends. 

Columbia Women's Freezer III Dress
Columbia Women’s Freezer III Dress, $47+
Short Sleeve Cold Shoulder Tunic
Long-Sleeve Cold Shoulder Tunic, $12.99
Wrangler Women's Retro Long Sleeve Western Denim Snap Dress
Wrangler Women’s Retro Long Sleeve Western Denim Snap Dress, $46
RVCA Women's Avery Woven Short Sleeve Dress
RVCA Women’s Avery Woven Short Sleeve Dress, $46+

Midi Madness

Midi dresses are a great style because they’re casual enough to wear for lunch out but classy enough to wear to a more formal occasion (think bridal or baby showers). When you match them with a new pair of cowboy boots and some statement pieces, you’ll even have the perfect ensemble for a Western wedding. This dress length is especially nice during the spring and summer when the days are getting warmer, but it hasn’t hit full heat yet. 

R.Vivimos Boho Midi Dress
R.Vivimos Boho Midi Dress, $29.99+
R.Vivimos Women's Long Sleeve Floral Print Retro V Neck Tassel Bohemian Midi Dresses
R.Vivimos Floral V-Neck Bohemian Midi Dress, $32.99
Smocked Elastic Waist Midi Dress
Smocked Elastic Waist Midi Dress, $49.99
Piece Dyed Denim Dress
Piece Dyed Denim Dress, $168

Long and Lanky

Long flowing dresses with classic western boots are the perfect way to bring out the country girl in all of us, making them a great way to escape the hustle and bustle of city life – if only in our minds. A long dress is a chic way to dress up a traditional pair of boots, so you can keep the casual look but remain elegant. And let’s face it: when you find a beautiful long dress made of a soft fabric that flows when you walk, it’s almost as good as finding the perfect pair of jeans, and you’ll find it hard to take it off at the end of the day. 

Sleeveless Maxi Dress with Pockets
Sleeveless Maxi Dress with Pockets, $37.99
Boho Beach Dress
Boho Beach Dress, $39.99

Best Boots for Your Buck

Boots are all one-size-fits-all; they come in a wide variety of colors, heel heights, and designs. If you like the traditional look, go for the full-height boots. Then have some fun selecting from a pointed or rounded toe. If you want a bit more summary style, consider a pair of mid-height boots or booties that will flatter dresses of all shapes, lengths, and styles. Then, kick up your heels and have some fun!

Durango Boots Crush
Durango Boots Crush, $195.50
ROPER Women's Riley Western Boot
ROPER Women’s Riley Western Boot, $46.50+
Ariat Casanova Western Boots
Ariat Casanova Western Boots, $269.95

Your go-to shoes may not be a pair of cowboy boots right now, but once you find a pair you love, they’ll become one of your favorite options. And finding fun dresses to wear with cowboy boots is an easier task than you might think, as evidenced by all of the beautiful options shown here. You’ll find that different types of dresses – from a simple dress to a floral dress to one with the perfect pop of color, will work well with a good pair of boots. This wardrobe combination will become a summer staple, allowing you to test new styles and different looks. 

Read Next:

Spring Dresses for Prime Women

Fashion Trends for Spring

Handbag Trends for Spring

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