What Men Should Wear With Cowboy Boots? [Styling Tips]

Looking for tips on what men should wear with cowboy boots?

There’s no question that cowboy boots are a stylish and timeless accessory for men, but not everyone knows how to style them correctly.

A simple rule of thumb is to pair your cowboy boots with similarly rugged clothing, such as items made from natural materials like denim, leather, and wool.

Boot experts, Ariat, recommend sticking to medium to dark-colored jeans with a bottom that fits over the top of the boots. (1)

Here, I’ll give tips on what to wear with cowboy boots so you can look your best. 

Key Takeaways

  • Cowboy boots are timeless pieces that can be worn in many different ways.
  • If you want to make a statement, go for a pair of brightly-colored cowboy boots.
  • Accessories are crucial to bring your look together.

CHECK: Best Cowgirl Boots for Riding Horses

Styles of Cowboy Boots

Before diving in further, let’s briefly go over the cowboy boot types so you can choose a pair that best suits your style.

Western Boot

The most common type of cowboy boot is the classic WESTERN boot.

different styles of cowboy boots

These boots typically have a pointed toe and a low heel. They’re often made from leather and can be either plain or embellished.

Roper Boot

Another popular style is the ROPER boot.

These boots are similar to Western boots but have a lower profile and a wider toe box. They’re usually made from suede or leather and can be found in various colors.

The Roper boot evolved from the Wellington, a British military boot that became popular when worn by Arthur Wellesley, 1st Duke of Wellington, in the early 19th century. (2)

Buckaroo Boots

This style of cowboy boots is less common but definitely worth mentioning.

Buckaroo boots have a higher shaft and a very wide toe box. They’re usually made from leather and can be either plain or embellished.

Cowboy Bootie

Finally, there’s the COWBOY bootie.

These short boots come up just above the ankle, as the name suggests. They’re a great option if you want the look of cowboy boots without all the coverage.

CHECK: Riding Boots With Steel Toe

Best Tops to Wear With Cowboy Boots 

Now that you know a little bit more about the different types, let’s move on to what men should wear with cowboy boots.

1. Denim Shirt

A denim shirt is one of the best tops to wear with western boots.

Casual shirts will give you that RUGGED look that goes perfectly with western-style cowboy boots. Plus, it’s a versatile piece that can be dressed up or down depending on the occasion.

2. Collared Shirts

Wearing a checked or plaid shirt with your western work boot is a great way to add a touch of sophistication to your look.

Opt for a button-down shirt in a cotton or linen fabric for different styles. This will keep you cool and comfortable while still looking sharp.

3. T-Shirt

For a more casual look, pair your cowboy boots with simple t-shirts.

Solid-colored or graphic tees are both great options. Just make sure the tee is fitted and not too baggy so it doesn’t look sloppy.

Pro Tip: This extremely comfortable look is the perfect pair for a weekend or running errands.

4. Leather Jacket

Another great option is a leather jacket.

A leather jacket will give you an EDGY look that goes well with cowboy boots. If it’s chilly, you can even layer a denim shirt underneath for extra warmth.

5. Wool Sweater

Finally, consider pairing your cowboy boots with a wool sweater, as it will keep you WARM in the colder months while still looking stylish.

Pro Tip: Be sure to choose a fitted sweater so it doesn’t look too bulky.

Best Bottoms to Wear with Cowboy Boots

Now that you know the best tops to wear with cowboy boots, let’s move on to bottoms.

1. Denim Jeans

As I mentioned, it’s best to choose rugged clothing made from natural materials when pairing it with most cowboy boots.

Bootcut jeans on denim are always a good choice. They come in VARIOUS styles, so you can choose a pair that best suits your taste.

Pro Tip: Opt for a darker wash for a more sophisticated look, or go for a light wash if you’re going for a more casual vibe.

For a great look with your cowboy boots, you need to size your jeans correctly. Check out this video for tips on how to do it:

2. Corduroy Pants

Another option is corduroy pants, which have a similar look and feel to denim.

Corduroy dress pants are IDEAL for fall and winter, as they’re made from a thicker material that will keep you warm.

Plus, they come in various colors, so you can find a pair that best suits your style.

3. Leather Pants

If you really want to make a STATEMENT, consider pairing your cowboy boots with leather pants.

Leather pants will give you a badass look perfect for a night out, especially with a pair of white cowboy boots.

Just be sure to AVOID wearing them in hot weather, as they can get quite uncomfortable.

4. Wool Pants

Finally, consider pairing your western boots with wool pants if you want to get COSY.

Wool pants keep you warm in the cold weather, and they have a rustic look that goes great with cowboy boots.

How to Accessorize with Cowboy Boots

In addition to choosing the right clothing, it’s also important to accessorize properly when wearing cowboy boots.

Adding the right accessories can take your outfit from ordinary to EXTRAORDINARY. Here are a few ideas to get you started:


A belt is a great way to ADD a pop of color or texture to your outfit.

Belt buckles come in various shapes and sizes, so you can choose one that best suits your style.


A scarf is another great way to add a pop of color or pattern to your outfit when you wear cowboy boots. Not only does a scarf keep you warm, but it also adds a touch of SOPHISTICATION.


A hat is a perfect way to top off any cowboy-inspired outfit.

Cowboy hats come in a variety of styles so that you can choose one that best SUITS your taste.

Pro Tip: If you’re not used to wearing hats, start with a smaller size so it’s not too overpowering.

A good fit is essential to top off your look with a cowboy hat. Find out how to fit your hat here:


Sunglasses are a must-have accessory for any season. They protect your eyes from the sun and add a touch of glamour to your look.

When choosing sunglasses, pick a pair that compliments your face shape.

Frequently Asked Questions

Can I Wear Shorts With Cowboy Boots?

Yes, you can wear shorts with cowboy riding boots. However, this generally only works well for women, and men should avoid it.  If you do want to try it, be sure to choose a pair of shorts made from a RUGGED material, such as denim or corduroy.

Will Skinny Jeans Be Flattering With Cowboy Boots?

Not really for men as the jean legs need to go inside the boots, but it can work well for women. Choose a pair of cowboy boots similar in color to your skinny jeans.
This will create a long, uninterrupted line that will elongate your body and make you look taller and slimmer.

How Do I Wear Cowboy Boots To A Formal Event?

For a more formal look, pair your western boots with dark-wash denim blue jeans and a button-down shirt. You can also add a blazer or jacket for extra sophistication.

Can I Wear Cowboy Boots to Work?

worn out cowboy boots

Yes, although not the typical work boot, cowboy boots can be worn to work as long as they are the right style to fit with casual clothing. Western work boots are a type of cowboy boot that is more appropriate for office wear. They are typically made from a softer leather and have a lower heel. 


Cowboy boots are a must-have in any fashion-savvy individual’s closet. They’re versatile, stylish, and, most importantly, they always look good.

When thinking about what men should wear with cowboy boots, you have tons of choices to change up your look from casual to formal.

No matter your style, there’s a way to incorporate cowboy boots into your wardrobe.

So next time you’re wondering what to wear with cowboy boots, remember these tips, and you’ll be sure to impress.

Cowboy standing in front of a mountain


1. How to Wear Cowboy Boots & Jeans – Men’s Style Guide | Ariat [Internet]. Ariat International. [cited 2022 Nov 28]. Available from: https://www.ariat.com/al/how-to-wear-cowboy-boots-and-jeans-men

2. Edwards A. The History and Lifestyle of Roper Cowboy Boots [Internet]. Dig This Design. 2019 [cited 2022 Nov 28]. Available from: https://digthisdesign.net/style-fashion/history-lifestyle-roper-cowboy-boots/

Ben R.
Ben R.

My name is Ben Roberts, and I absolutely love animals. So, naturally, I love writing about them too! I have three dogs and one old cat, plus experience with horses. Each one of them provides me with a new adventure every day. And the best part is they’re all best friends. Well, except the cat when he gets a little annoyed. FIND HIM ON: TWITTER.
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