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

Since the late 1800s, this rugged style of footwear has embodied the spirit of freedom and individuality in the West. Now it’s the first port of call for cowboys returning to their roots and apparel-conscious men who want to stand out from the crowd.

You may wear cowboy boots with a simple t-shirt and jeans for a casual, authentic look. You can also choose to wear different hues of denim on top and bottom or choose one shade and incorporate it into both the upper and lower portions of your outfit. Your jeans must skim the top of your boots and not fall above the shoes’ collars.

If you’re never bucked a bronco or straddled a horse, fear not. We’ve got all the tips, tricks, and techniques to look like a hard-riding, long-range cowboy — without ever having been on horseback.

How to Wear Men’s Cowboy Boots with Jeans?

Jeans and boots come in different styles, cuts, and colors. The only thing you need to consider is what looks best on YOU!

If you wear cowboy boots with jeans, don’t muck it up.

The ideal pair of jeans to be worn with cowboy boots should be hemmed to the correct length, have a comfortable cut, and come in a color that complements your boots. I wrote a detailed article about the best men’s jeans to wear with cowboy boots. To read that article, click here.

Jean Length

Wear cowboy boots with fitted jeans that are tight from hips to thigh but loose on the leg so that the boots have enough room.

Your jeans should reach the top of your feet and stop at your heels. They should be long enough to protect your legs but not so long that they drag on the ground, allowing debris and other things to get caught in them.

Jean Cut

Wearing cowboy boots with jeans requires an understanding of the cut of jeans that is being worn. Cut refers to the height of the jeans or where it reaches on your legs.

The cut of each pair of jeans will determine how well they’ll work with cowboy boots.


Bootcut jeans and cowboy boots are like night and moon. The jeans fit from the waist down to the knees, where they flare out enough for the shaft of your cowboy boots to be tucked underneath.

Straight Cut

Straight-cut jeans also pair effortlessly with cowboy boots, but they’re not as wide at the knee as bootcut jeans. As a result, you may have some difficulty fitting them over the boots’ shafts.

Jean Color

The color of your jeans depends on your personal style, but you need to know the basics of how to match them with cowboy boots if you want to achieve the look you’re going for.

Dark blue and charcoal-washed are the best colors of denim, hands down. Medium blue denim works great for daytime wear, and the darker-washed denim conveys an air of maturity, which you’ll want on a night out.

Across the pond, light-colored denim is a fine example of the traditional roots of this modern-day classic. Its faded wash and subtle distress mark whisper “retro,” and who doesn’t love to hear that?

Are Men’s Cowboy Boots in Fashion?

Today, men’s cowboy boots are wardrobe essentials for ranchers, construction workers, designers, celebrities, and social media influencers who use the boots to project an image of masculinity.

Arnold Schwarzenegger, famous for his masculine body and starring in the “Terminator” films, often wears cowboy boots. He is such a big fan of these boots that he has a collection of them.

From Adam Selman’s rustic pair to A$ap Rocky’s Calvin Kleins, cowboy boots have been spotted on the feet of fashion trendsetters during the 2017 CFDA Fashion Awards and at the Met Gala.

Can You Wear Cowboy Boots with Shorts?

Although cowboy boots and shorts may seem like a natural match for men, they do not go well together. The best look is a pair of boots with standard-cut or boot-cut jeans. Khakis with boots can also be trendy; it just depends on the rest of the outfit. They also look nice when used to complement a suit.

While women can wear cowboy boots and shorts in a variety of styles, men are limited to jeans or khakis with their boots. That being said, if you want to wear a combination of cowboy boots and shorts, your personality must be strong enough to channel the breeziness of such a look.

How to Wear Short Cowboy Boots?

Short cowboy boots—also known as roper boots— were specifically designed to perform in the rugged work environment of a ranch but have since been transformed into voguish pieces by the forces of fashion.

Cowboy Look

You can nail this classic cowboy look with a white t-shirt, a flannel, dark denim, and a solid leather belt.

CEO Look

A pair of cowboy boots, when styled impressively, will lend your outfit the sharpness fit for a CEO. To maintain that traditional feel, stick to darker colors of suits and boots.

Add an exotic element to your attire with cowboy boots made from exotic leathers such as snakeskin or alligator hide, or ostrich skin. You can find many of these at Ariat and Rods.

Business Casual Look

This outfit is the perfect mix of formal and casual, allowing you to dress for success with your work and social life. In order to pull off this look, pair your short cowboy boots with a collared t-shirt and confidence.

Construction & Tradesmen Look

The cowboy boot has been the choice of ranchers for hundreds of years. It makes sense, then, that construction workers would turn to cowboy boots as safe and comfortable footwear on the job.

If you are in the market for a pair of steel-toed safety cowboy boots, check out Ariat, Irish Setter, and Rods. Each of these companies offers a wide selection of men’s safety cowboy boots.

Can You Wear Cowboy Boots with Jeans?

Absolutely! Wearing jeans with your boots is a subtle way of showing your love for the Wild West and all its traditions. There are a lot of styles of jeans available, so you can pick whatever shade and cut suit you best.


The best way to look like a cowboy is to have an authentic wardrobe that is well thought out and executed. Then before getting dressed, you need to know how to put together a good outfit, which involves more than just how you layer your clothing and how you choose your colors – it also consists in choosing some cowboy boots.

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