How To Wear Cowboy Boots (A Men's Guide)

A man doesn't need to be a cowboy to wear cowboy boots. Though these boots are primarily worn for cattle work, wearing cowboy boots has been a popular fashion trend for many years now.

Cowboy boots are classic footwear rooted in the rich history of cowboys centuries ago and until the present. After you’ve worked them in, they can be the most comfortable boot that you own.

The most authentic and casual style when wearing cowboy boots is to pair them with a t-shirt and denim jeans. If you prefer an overall denim look, you may choose a different denim hue for the top and a different one from the bottom. Your jeans must rest above the heel of your cowboy boots.

There is always a great impression of seeing a man wearing cowboy boots. If you are one of those who wants to have a cowboy look but haven't ridden a horse, well, this article is for you. This guide is a very easy and detailed guide to rock that cowboy outfit with confidence.

How to Wear Men's Cowboy Boots with Jeans?

There are so many different cuts for jeans and other styles of cowboy boots, and you won't have any problem styling it out. The only thing you need to consider is your personal preferences. 

When you wear cowboy boots with jeans you must find the right combination that will get you on track. 

Things to consider are the correct jean length, the right cut, and the color of the jeans being paired with your cowboy boots. (I wrote a detailed article about the best men's jeans to wear with cowboy boots, to read that article click here.)

The classic style includes pairing your boots with bootcut jeans.

Wrangler Authentics Men's Classic 5-Pocket Regular Fit Jean, Twilight Flex, 34W x 32L

Men's Regular Cut Wranglers, Compare pricing:
Amazon vs. Wranglers vs. Zappos
(To find the best price and selection, check all three links)

Jean Length

When wearing cowboy boots with jeans, it is recommended that you should choose a pair of jeans that are fitted from hips to thigh but are loose enough on the leg part to provide space for the boots. 

Your jeans must be long enough to protect your legs but must not be too long to drag in the dirt. 

The purpose of your jeans is to protect your legs and should come down to rest on the top of your foot and down toward the heel without reaching the ground.

Jean Cut

When wearing cowboy boots with jeans, it is necessary to consider the cut. 

It is good to know the differences of each for you to choose your preference.


Levi's Men's 517 Boot Cut Jean, Medium Stonewash, 34x32

Levis Boot Cut Men's Jeans, Compare pricing:
Amazon vs. Levis vs. Zappos

Boot-cut jeans and cowboy boots are the perfect pairs. It has a perfect fit from the knees upward and has a flared cut from the knees down the end. 

This cut is enough to tuck the cowboy boots shaft into the jeans.

Straight Cut

Ariat Men's Flame Resistant M5 Slim Fit Straight Leg Jean, Shale, 32W x 32L

Ariat, Atrait Cut Men's Jeans, Compare pricing:
Amazon vs. Ariat vs. Zappos

Straight-cut jeans are also a good choice to pair with your cowboy boots. However, the cut from your knees going down is not that wide compared to the boot cut. 

It may take a little effort to get your jeans over your upper boot. 

Typically, men don't tuck their jeans into their cowboy boots...

Jean Color

The color preference depends on your personal style, but you need to have a little idea of how to match your jeans with cowboy boots to reach your desired look. 

The best color of denim is dark blue and charcoal washed.

 The medium blue denim is suitable for daytime use, and the darker one is good for night-outs. The lighter-colored denim gives a retro-looking style.

Are Men's Cowboy Boots in Fashion?

Men's cowboy boots are absolutely in fashion, they are a classic "manly" footwear that will likely never go out of style. For rodeo footwear, cowboy boots are a wardrobe staple. Ranchers, construction workers, designers, celebrities, and even social media influencers have been seen rockin' cowboy boots.

The legendary star Arnold Schwarzenegger is often seen in his cowboy boots. His rodeo-styled outfit became a trend giving an impression of masculinity. Arnold has a collection of cowboy boots. 

Not only do cowboy boots showcase masculinity, but they also showcase fashion. 

In the 2017 CFDA Fashion Awards, Adam Selman was spotted wearing rustic boots. Asap Rocky was also spotted wearing Calvin Klein boots at the Met Gala. 

These styles give a modern look to men's cowboy outfits.

Can You Wear Cowboy Boots with Shorts?

For guys, cowboy boots and shorts aren't recommended.  The best look for a man is to wear cowboy boots with standard cut or boot cut jeans. A man can get away with cowboy boots and Khakis, but don't tuck them in. Cowboy boots also look good complimenting suit. 

Square Toe Men's Cowboy Western Boots in Genuine Leather by GadwallAR

Men's Square Toe Cowboy Boots, Compare pricing:
Amazon vs. Ariat vs. Zappos

Ladies can get away with cowboy boots and shorts, but I'd say no to the guys.

Men are not as lucky as women who can wear anything with cowboy boots. Pairing cowboy boots with shorts will not cater to the masculine style. 

However, if you prefer to wear your boots with shorts, your going to create a unique trend. You may have the personality to get away with it.

If you think pairing cowboy boots with shorts is your style, then go for it. 

How to Wear Short Cowboy Boots?

Short cowboy boots or roper boots are functionally developed for cattle work and not necessarily for fashion. However, due to the fashion evolution, they have also been worn as fashion wear for decades now. 

Let's discuss different ways to wear short cowboy boots... 

Cowboy Look

WOLVERINE Men's Rancher ST Work Boot, Dark Brown/Rust, 10

Wolverine Cowboy Boots, Compare pricing:
Amazon vs. Wolverine vs. Zappos

To complete this look perfectly, you need to combine a white t-shirt and a flannel. You also need to wear dark denim with a solid leather belt. This combination will showcase the classic cowboy look.

CEO Look

CEO look is considered a significant upgrade in wearing cowboy boots. If you want to have a formal look, you can pair your boots with a business suit.

Laredo Men's 68067 Monty Western Boot,Black / White,7 D US

Wolverine Cowboy Boots, Compare pricing:
Amazon vs. Ariat vs. Zappos

To maintain that traditional look, just make sure to stick with darker colors of suit and boots.

You could choose a pair of cowboy boots with an exotic leather such as snakeskin or alligator, or ostrich leather. Find these boots at Ariat or Rods or

Business Casual Look

This outfit is between formal and informal look. To bring the elements of it, you can pair your short cowboy boots with a collared t-shirt.

Durango Men's DB594 11" Harness Boot Distressed Brown 11 D - Medium

Durango Harness Distressed Cowboy Boot, Compare pricing:
Amazon vs. Rods vs. Zappos

Whatever your fashion preferences might be, make sure to wear these outfits with confidence. The business casual look will showcase a typical cowboy personality and lead you to a successful wardrobe pull-off. 

Construction & Tradesmen Look

Cowboy boots have been the go-to choice for ranchers for hundreds of years. It just makes sense that men (and women) in construction would turn to cowboy boots as a safe and comfortable footwear on the job.

Irish Setter Work Men's 83912 Marshall 11" Pull-On Steel Toe Waterproof Work Boot,Brown (medium and light brown),15 D US

Irish Setter Steel Toe Cowboy Boots, Compare pricing:
Amazon vs. Irish Setter vs. Rods

There are many companies that offer steel-toed safety cowboy boots. I am partial to Ariat, Irish Setter, and Rods. They each have a fantastic selection of men's safety cowboy boots.

Can You Wear Cowboy Boots with Jeans?

Absolutely yes! You can wear cowboy boots with jeans. Pairing your cowboy boots with pants always caters to rodeo culture and functional clothing. This combination speaks of a classic and authentic cowboy style.

There are a lot of designs for jeans that you can pair with your cowboy boots. You can wear any combination to express your preference and personality.  


Now and then, cowboy boots fashion is in and out. Though the functions of this footwear are designed for ranch work, this has evolved into a fashion trend. This classic and authentic look also showcases the history of rodeos. 

To pull off your desired cowboy-style right combination is essential. Not only does this outfit suggest masculinity and a macho look, but it also suggests a specific personality of a person who wears it.

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