20 Fashionista Tips: How to Wear Cowboy Boots in the Summer

Written by Marie A.

Women’s fashion trends (and common sense) may have you asking: “Boots in the summer, yes or no?”

A pair of quality cowboy boots on a woman speaks volumes about her, whether she realizes it or not. It says that she’s easygoing, fun, and adventurous; she’s up for almost anything that comes her way.

It also says she’s got a great sense of fashion, especially when pairing those versatile boots with her summer wardrobe. She’s creative with her choices, and she doesn’t have to be told she looks fabulous (though it’s always appreciated).

Want to know how to be a fun-loving, fashion forward female with cowboy boots strapped on during the hottest time of year? Here are a few tips, starting with a little reminder of our simple guidelines. 

Do Don’t
  • Wear what makes you confident
  • Pair boots that have a busy design with a busy outfit
  • Remind yourself that leather is capable of being both cool and hot
  • Think of boots as only a casual footwear choice
  • Remember, denim isn’t a boot’s only friend
  • Forget to consider the boot sole and what it’s best suited for (e.g. dancing, working)
  • Pair your boots with lightweight fabrics
  • Forget that cowboy boots come in a ton of sizes, widths, and heights

Now, let’s get into the details. What outfits work best with cowboy boots in the summer? There are four summer fun categories below, and you can check out our Pinterest board for more examples of each.

Wear With a Dress

This classic pairing is what fashion dreams are made of. Dresses come in a variety of cuts, colors, lengths, and textures – just like cowboy boots.

A light and breezy dress coupled with a pair of cowboy boots can be something dressy, casual, flirty, and so many other things. 

And, don’t think for a second that you can’t pair cowboy boots with a dressier, simpler dress. It’s all about balancing the fashion of the boot with the perfect amount of detail in the dress.

Click to see it on Amazon

Doing it Right:

  • Add drama to the look with fringe.
  • Pair your dress with some form of denim – either a vest or the dress itself – to give a beautiful silhouette.
  • Put the outfit together with balance in mind; busy prints on top and bottom take away from each other.

Doing it Wrong:

  • Don’t put plain boots with a plain dress and expect it to pop; there should be something to draw the eye in.
  • Whatever length your dress is, take it into consideration when pairing with a boot. Don’t pair tall boots with a long dress.

Perfect Pairings:

Some of our favorite dresses for this look are:

Want more inspiration? Visit our Pinterest board for some great examples of cowboy boots with summer dresses!

Wear With Cutoff Shorts

When it comes to cutoff shorts, this is what most people imagine when they think of cowboy boots in the summer.

Daisy Duke made this look famous, and you can up the sexiness or downplay it, depending on your level of comfort.

It’s the quintessential outfit for anyone who wants to wear cowboy boots, and it’s the easiest to pull off. And the shorts can come in any color, much like your boots!

Click to see it on Amazon

Doing it Right:  

  • Pair your cutoff shorts with a long cardigan. Bonus points for lace details!
  • Use a belt to match the leather and tie the outfit together.
  • Put the outfit together with balance in mind; busy prints on top and bottom take away from each other.

Doing it Wrong: 

  • Don’t go into this look thinking it’s only for the slimmer body types.
  • The main way to go wrong with this look is wearing something that doesn’t make you confident.

Perfect Pairings:

Some of our favorite cutoff shorts for this look are:

Want more inspiration? Visit our Pinterest board for some great examples of cowboy boots with cutoff shorts!

Comfortable Cowboy Boots

Wear With a Romper

A romper is the perfect blend of dress and cutoff shorts, which means it’s perfect for cowboy boots.

This combination can be as chic as your best dress, or as casual as your cutoff shorts.

You can’t go wrong with this outfit in the summertime.

Click to see it on Amazon

Doing it Right:  

  • Add leather to your outfit with a cute clutch.
  • Choose boots that have some color that matches any prints on your romper to make it all come together.
  • Add a decorative C4 Belt to pull it all together without taking away from the look.

Doing it Wrong:

  • Don’t think that this look only works with solid colored rompers.
  • You don’t have to only go with the standard romper; maxi dress rompers are perfect for cowboy boots, too.

Perfect Pairings:

Some of our favorite rompers for this look are:

Want more inspiration? Visit our Pinterest board for some great examples of cowboy boots with summer rompers!

Wear With Light Leggings or Jeans

At night, things cool off. But that doesn’t mean your outfit has to lose its heat.

Create a perfect casual or formal look with leggings or jeans.

Pair your cowboy boots (or booties) with leggings and a beautiful skirt or shorts to skip the chill that sometimes come in the night air.

Click to see it on Amazon

Doing it Right:

  • This look is perfect for booties!
  • Distressed jeans are great for this look.
  • Add a hat to complete the look.

Doing it Wrong:

  • Simple black leggings aren’t your only option.
  • Don’t overdo it on the texture and patterns of boots, leggings, and top.

Perfect Pairings:

Some of our favorite leggings and jeans for this look are:

Want more inspiration? Visit our Pinterest board for some great examples of cowboy boots with light leggings and jeans!

Accessorize Your Look

Find new ways to pull everything together by adding some flair to your cowboy boots in a subtle way.

  • Match the leather. One way is by pairing the leather of the boots with a similar leather in your outfit, like a purse, clutch, or a belt.
  • Another great accessory is a cardigan. It can be either long or short, depending on what you’re pairing it with. We suggest adding drama to your look by pairing short rompers or shorts with a long cardigan with lace details.
  • The final topping piece on a great cowboy boot outfit in the summer is a hat. Whether it’s a fun floppy hat or a simple fedora, this accessory is sure to pull attention to your beautiful face while protecting you from the sun.

Want more inspiration? Visit our Pinterest board for some great examples of cowboy boots with summer outfits!

Bonus: 10 Best Cowboy Boots for Hot Weather

Not sure where to start looking for great summer cowboy boots? Try one of our favorites below!

  1. Ariat Ladies Quickdraw
  2. Tony Lama Ladies Black Label Tan Boots
  3. Justin Ladies Bent Rail Damiana Boots
  4. Lane Boots Women’s Dove Ankle Boot
  5. CORRAL Women’s Eagle Sequence Inlay Western Boots
  6. Lucchese Women’s M4920 Item
  7. CORRAL Women’s Bronze Fringe Studded Ankle Boot Snip Toe
  8. Lane Boots Women’s Dawson
  9. Corral Women’s Juliet Deer Skull Overlay Floral Embroidery Cowgirl Boots
  10. Lane Women’s Plain Jane Cowgirl Boot Round Toe

Frequently Asked Questions

What is the best brand of cowboy boots?

This is like asking someone their favorite color. You’ve got a preference, but they vary by individuals. That being said, you can’t go wrong with Justin Boot or Ariat.

They’re some of the best for a reason, and they have plenty of price points to choose from.

Is it OK to wear boots in the summer?

It’s always acceptable to wear boots! Leather has the added benefit of being cool when it’s hot and hot when it’s cold.

Boots are the most versatile of the shoe world.

What can I wear cowboy boots with?

Dresses, rompers, anything can go with the right cowboy boot. Be as adventurous as you dare, and know that there are really not any limits.

What are the best cowboy boots for the money?

Check out Justin Boots! (They last a very long time, too.)

Can you wear boots year round?

In a word, yes. They’re designed to be worn by cowboys through the coldest months–and the hottest.

How can I stretch the top of my cowboy boots?

Livestrong has a great recipe and step by step guide to stretch boots.

However, if you have wide calves, there are cowboy boots out there for you. You just have to look for them. Some of our favorites listed include wide calf sizes.

Are square toe boots in style?

The square toe boot may come and go, but right now, it’s definitely in style. While square-toed cowboy boots are often popular for people with wide or flat feet, this trend has also taken over women’s fashion.

Comfort may play a part in this trend, as a square toe often gives your foot more room to breathe. A square toe is also more flexible and can go with more looks, from business casual to a night on the town.

How to wear over-the-knee cowboy boots?

While an over-the-knee cowboy boot isn’t a true cowboy boot, they’re cute, comfortable, and work with a range of outfits (just not so much for riding).

Skinny jeans or leggings are one way to go, as both options can fit inside the shoe. Choose this option if the boot has a design you want to show off.

Another way to style these boots is with a mid-thigh skirt or dress. You’ll see a little bit of your thigh, but your legs are largely covered thanks to the height of the boots.

How do you wear cowboy boots in the summer for men?

Cowboy boots for men can be part of casual outfit (jeans, button up, polo kind of outfit) or a more formal outfit (think of a suit and go from there). The leather of the boots is all you’ll see when paired with boot cut jeans.

Check out our 10 Best Cowboy Boots for Men!

How do you wear short cowboy boots with jeans?

The same way you would if you had leggings on. If you’ve got boot cut jeans, then you’re still in luck. You can wear them draped over the boot.

Boyfriend style? No problem! Roll them up to right above the top of your best pair of booties.

What are the best cowboy boots for walking?

Check out our article on the best cowboy boots for walking.

Where can I find more western dresses to wear with boots?

Check out our article on the best western dresses to wear with boots.

Summer Fashion Forward

Cowboy boots are made to be versatile. They add a sense of adventure and fun to any outfit, and they’re the most treasured shoe in a wardrobe – no matter the season!

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About the author


Marie A.

Though I love all horses, Arabians are my all-time favorite breed! I'm raising an Arabian filly and riding and showing my gelding on the Class A Arabian Circuit. I also enjoy going to horse racing and following the latest industry news.