How to Style Cowboy Boots Men – Tips and Tricks

Understanding Cowboy Boots

Cowboy boots are a staple in men’s fashion, and knowing how to style cowboy boots can elevate any outfit. To start, it’s important to understand the different styles of cowboy boots available.

There are traditional styles, such as the classic Western boot, as well as more modern variations, such as the roper or square-toe boot. Additionally, cowboy boots can be made of various materials, including leather and exotic skins.

When it comes to styling cowboy boots for men, there are a few key considerations to keep in mind. Firstly, it’s important to choose the right boots for the occasion and your personal style.

A more traditional Western boot can be dressed up or down, while a more modern style may be better suited for casual wear.

Color matching is also crucial when it comes to styling cowboy boots. Opt for a pair that complements the rest of your outfit, whether that means coordinating with your shirt or jacket, or even matching your belt and accessories.

In terms of clothing options, cowboy boots can be paired with a range of outfits. Slim-fit jeans or chinos work well for a casual look, while a tailored suit can be paired with more traditional Western boots for a formal event.

For a rugged, outdoorsy look, pair your cowboy boots with a flannel shirt and a denim jacket.

Finally, grooming is essential when it comes to styling cowboy boots. Make sure to keep your boots clean and well-maintained to show off their unique style and high-quality materials.

According to Esquire, cowboy boots are a versatile addition to any man’s wardrobe, and can be styled to suit a variety of occasions and personal styles. By understanding the different styles of cowboy boots available, color matching, and grooming tips, any man can rock this classic footwear with confidence.

Remember, how to style cowboy boots men depends on your personal preferences and the occasion, so have fun experimenting with different looks!

Check out this Youtube video on how to style cowboy boots for men if you want to elevate your rugged fashion game.

Classic Western Boots

If you want to style classic western boots for men, the most essential thing to keep in mind is the fit. These boots are meant to be snug, but not too tight on the feet.

Stick to a neutral color palette such as brown or black and pair them with jeans or khaki pants for a classic look.

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For a more formal occasion, you can wear these boots with a suit, but make sure the pants are tailored to fit over the boots and not bunch at the ankle. Overall, classic western boots are versatile and easy to style for any occasion.

Western Work Boots

If you want to style your cowboy boots for outdoor activities and ranch work, western work boots are the perfect choice for you. These boots are designed to be rugged and durable, with a thick sole and a round toe that can withstand tough environments.

You can pair them with jeans, a plaid shirt, and a cowboy hat for a classic western look.

When it comes to color, brown and tan are popular options that look great with a variety of outfits. You can also choose boots with a distressed finish for a more worn-in look.

Just make sure to keep them clean and conditioned to maintain their durability and appearance.

Overall, western work boots are a great choice for men who need sturdy and comfortable boots for outdoor activities and ranch work. With the right outfit, they can also be a stylish addition to your wardrobe.

Buckaroo Boots

If you want a more contemporary cowboy look, go for Buckaroo boots. These boots have a higher shaft and elongated toe, making them perfect for fashion-forward men.

To style Buckaroo boots, pair them with skinny jeans or slim-cut pants. You can also wear them with shorts and a button-down shirt for a more relaxed vibe.

As for the top, a plaid shirt or denim jacket can complement your boots well. Don’t be afraid to experiment with colors, just make sure they match your outfit.

Finally, accessorize with a hat and belt that complement the boots to complete your cowboy look.

Roper Boots

Roper boots are versatile and can be styled for both formal and casual occasions. For a more formal look, pair them with dress pants and a blazer.

For a casual look, wear them with jeans and a button-up shirt. Don’t be afraid to experiment with different colors and textures to add a unique touch to your outfit.

How to Wear Cowboy Boots Men

Pairing Cowboy Boots with Jeans

The perfect way to style cowboy boots men with jeans is by pairing them with a straight leg fit. Avoid baggy or skinny jeans as it can ruin the look.

Also, make sure the jeans are long enough to cover the boots slightly. Rolling or cuffing the jeans is a big no-no as it can break the visual line produced by the boots.

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Cowboy boots men and jeans - how to style cowboy boots men

Choosing the Right Pant Cuts for Cowboy Boots

When it comes to choosing pants to pair with cowboy boots, there are a few cuts that work well. Bootcut and flared pants are great options since they complement the shape of the boots.

Straight-legged pants can also work, but make sure they’re tailored to fit well around the boots. Avoid pants with a narrow leg opening, as they won’t allow the boots to shine.

Opt for pants with a wider opening to show off your stylish footwear.

Color Matching with Cowboy Boots Men

When it comes to color matching with cowboy boots, it’s best to stick with neutral and earth tones such as black, brown, grey, and dark blue. These colors work well with all types of cowboy boots and can add a touch of sophistication and masculinity to any outfit.

Avoid wearing bright colors and busy patterns which can overwhelm the boots and ruin the overall look. Instead, opt for solid colors or muted patterns that accentuate the boots without stealing attention from them.

For example, pair a brown cowboy boot with dark jeans and a green button-down shirt for a simple yet stylish look.

Styling Tips for Cowboy Boots Men

Understand When to Wear Them and When Not to Wear Them

Cowboy boots are not suitable for all occasions. They may not be appropriate for formal events such as weddings, business meetings, or black-tie events.

Stick to casual occasions, parties, and outdoor activities when wearing cowboy boots.

Cowboy boots are a versatile piece of footwear that can add a Western vibe to any outfit. However, it is important to understand when and where to wear them.

Firstly, cowboy boots are not suitable for formal events such as weddings, business meetings, or black-tie events. These occasions call for more formal footwear.

On the other hand, cowboy boots are perfect for casual occasions, parties, and outdoor activities such as horseback riding or hiking. When dressing up a casual outfit with cowboy boots, consider pairing them with jeans, a button-down shirt, and a cowboy hat.

Accessorize with a Hat or Belt

If you want to add an extra touch of authenticity to your cowboy boots men outfit, try accessorizing with a matching cowboy hat or belt. This is a classic look that never goes out of style.

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To make sure the hat or belt matches the boots, make sure to choose a similar color or material. Additionally, make sure the rest of your outfit is understated, so that your boots, hat, and belt are the focal point of your look.


Based on, there are various ways on how to style cowboy boots men. One way is to pair them with well-fitting jeans, like straight-leg or boot-cut styles, and choosing dark-toned jeans for a sleek appearance.

It is also recommended to avoid tucking the jeans into the boots to keep the focus on the boots. Another popular option is to style cowboy boots with comfortable khakis, chinos, or linen pants for a casual and relaxed look.

Remember to consider the style, material, color, pant cut, and occasion before choosing the right cowboy boots to wear with your outfit.


Frequently Asked Questions

What do men wear cowboy boots with?

Men can wear cowboy boots with plain white dress shirts, as well as more patterned, casual shirts. Close-fitting, black jeans are preferable than light blue jeans worn for work. For obvious reasons, a boot-cut style is a must-have. Only tuck your pants into your boots if you're really working on horseback and need to.

Do cowboy boots go over or under jeans for men?

In most scenarios, men should wear jeans over their cowboy boots. However, there are some occasions when it's appropriate to tuck your jeans into your cowboy boots. Women, on the other hand, can wear skinny jeans or leggings inside their cowboy boots to show off their footwear.

How to wear cowboy boots with jeans for guys?

As a general rule of thumb, we recommend wearing medium to dark-wash jeans over your boots (not tucked in). The jeans should be fairly form-fitting in the upper legs but have enough space in the lower leg to accommodate the boot, without showing an outline.

Is it OK to wear skinny jeans with cowboy boots?

Yes, it is okay for men to wear skinny jeans with cowboy boots. A classic combo with a modern twist, skinny jeans + cowboy boots allow men everywhere to show off every inch of their favorite pair- not just the toe!

Jonathan B. Delfs

I love to write about men's lifestyle and fashion. Unique tips and inspiration for daily outfits and other occasions are what we like to give you at Do you have any notes or feedback, please write to me directly: [email protected]

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