What to Wear with Cowboy Boots Men’s: A Style Guide

Cowboy boots have been a staple in American fashion for centuries, but many men struggle with finding the right outfit to wear with them. In this style guide, we’ll give you tips and ideas on what to wear with cowboy boots men’s to look fashionable and put together.

If you’re planning to wear cowboy boots, it’s important to choose the right outfit that complements these classic shoes. According to gq, one trend for men is pairing cowboy boots with slim-fit jeans or chinos and a plaid shirt.

This look is perfect for casual events or a night out with friends. Another great option to wear with cowboy boots men‘s is dressing it up with a blazer and dress pants.

According to the Fashion is to, you can complete the look by wearing a crisp white shirt and a Western-style belt. This ensemble is perfect for a wedding or formal event.

If you’re feeling adventurous, you can try styling cowboy boots men‘s with shorts. Shorter shorts work best, and you can pair it with a simple white T-shirt or a button-down shirt.

This look is perfect for summer events or a day out with friends. In conclusion, there are plenty of outfit options to wear with cowboy boots men’s.

From casual to formal occasions, you can make these classic shoes work with different styles. Just remember to stick to the basics, and you’ll look fashionable and put together.

Whether you’re going for a rugged, Western vibe or a classic preppy style, your cowboy boots should complement your outfit and showcase your personal style.

Check out this Youtube video if you want to learn how to rock cowboy boots with style and confidence, and take your fashion game to the next level: “Stop Wearing Cowboy Boots Wrong (How To Rock Western …)”

Cowboy Boots and Denim

When wearing cowboy boots, pairing them with jeans is the perfect combination. To create that stylish look, here are some tips on how to pair cowboy boots with denim:

  • The Best Denim Color for Cowboy Boots and Jeans – Dark wash denim is an ideal pair for cowboy boots. This type of denim can complement any color of boots making you look great and fashionable.
  • Cowboy Boots and Jeans: Finding the Right Length – It is important to find the correct length of jeans when wearing them with cowboy boots. The jeans should fit snugly around your hips with a shorter hemline to show off the boots.
  • How to Wear Cowboy Boots With Jeans – The key to wearing cowboy boots with jeans is to tuck the jeans into the boots. This highlights the boots and accentuates the overall look of your attire.
  • The Best Pant Cuts for Cowboy Boots – Bootcut jeans are the most preferred choice when wearing cowboy boots. The flare at the bottom of the jeans compliments the boots and allows for more space to show off the design of the boots.

Remember that cowboy boots are versatile footwear that can be paired with various types of clothes to create different looks. By following these tips, you can create the perfect cowboy boots and denim ensemble that will never go out of style.

Dress Clothes and Cowboy Boots

If you’re wondering which dress clothes go with cowboy boots, you’ll be glad to know that cowboy boots can be worn with a variety of dress clothes for a formal look with a twist.

  • Pair your cowboy boots with a suit or blazer to create a bold and unique look. Choose a darker color suit such as black or navy, which pairs well with brown or black boots.
  • For a semi-formal look, wear your cowboy boots with a dress shirt and dress pants. You can also add a stylish vest or cardigan to complete the look.
  • When choosing dress clothes to wear with cowboy boots, be sure to choose high-quality clothes that fit well.

According to Country Outfitter, “The key here is to make sure your look is balanced. There is already so much going on with cowboy boots that you don’t want to look like a hot mess.

A model wearing a suit with cowboy boots - what to wear with cowboy boots men's

When it comes to casual wear for men, cowboy boots can add some style to your outfit. One great way to wear cowboy boots is with a simple T-shirt and jeans.

This simple combination can make you look fashionable while still being comfortable.

Another option is to pair your boots with a plaid shirt. The colors in the shirt can complement the boots and add some depth to your outfit.

For a more classic look, try wearing your cowboy boots with a denim shirt. This pairing can create a timeless, rugged look that is perfect for any casual occasion.

If you prefer a more modern look, skinny jeans can be paired with cowboy boots for a trendy, fashionable outfit. The slim-fit jeans provide a nice contrast to the chunky boots and creates a sleek silhouette.

Remember, cowboy boots can be versatile and can be worn in many different ways. Experiment with different outfits to find the perfect combination that suits your style and personality.

Types of Cowboy Boots and Materials

Cowboy boots have different types, each possessing a unique style. The most common types of cowboy boots are classic Western boots, Western work boots, Buckaroo boots, and Roper boots.

Classic Western boots are the most popular of all the types. They are known for their pointed toes and a high shaft.

Western work boots, on the other hand, are more reinforced and durable than the classic ones. They are designed for ranch and farm work, and they come in different leather materials.

Buckaroo boots are much taller than the classic ones. It has a high shaft that is ideal for riders who need added protection.

Roper boots are the most comfortable of all cowboy boots. They have a round toe and a shorter shaft than the classic ones.

When choosing a pair of cowboy boots, it is essential to decide on the right material. Leather is the most common material used for cowboy boots.

It is durable and long-lasting. Exotic leather materials such as alligator, ostrich, and snake skin are also becoming popular materials.


Different types of cowboy boots - what to wear with cowboy boots men's

Tips and Tricks

When wearing cowboy boots, it’s important to know how to style them perfectly. According to Country View Western, pairing your boots with a classic t-shirt and denim is a great go-to look.

For a relaxed, effortless outfit, wear your jeans over your boots instead of tucking them in. This simple tweak will make your appearance more put-together and sleek.

Cowboy boots with jeans - what to wear with cowboy boots men's

Remember to pair your cowboy boots with a classic t-shirt and denim jeans for a relaxed and effortless look. Always wear your jeans over your boots, not tucked in.


Pairing cowboy boots with the right outfit can be effortless with the right combinations. To achieve a laid-back look, pair your boots with a classic t-shirt and denim jeans.

Always wear your jeans over your boots to give your look a more put-together appearance. Don’t be afraid to experiment with different outfits to find the perfect match for any occasion.


Frequently Asked Questions

What's the best thing to wear with cowboy boots?

To wear your cowboy boots for a night out on the town, pair them with a dark pair of jeans, a solid colored shirt, and a bomber or Harrington jacket.

Do cowboy boots go over or under jeans 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.

Is it OK for men to wear cowboy boots with shorts?

Modern cowboy boots aren't just for riding. Now, they can be worn with dresses, shorts, or even a suit. But don't skimp on your purchase.

How are cowboy boots supposed to look with jeans? How do you wear cowboy boots with jeans?

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.

What jacket to wear with cowboy boots for men?

To wear your cowboy boots for a night out on the town, pair them with a dark pair of jeans, a solid colored shirt, and a bomber or Harrington jacket. Try a blazer for a smart-casual look, or give yourself an edge with a T-shirt and leather jacket.

Can any guy wear cowboy boots?

You don't have to be a cowboy to wear and appreciate Western boots. Although you'll get more use out of them if you take up Western dancing and rodeo — a man can enjoy a touch of Western style in his outfits now and again.

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 MensVenture.com. Do you have any notes or feedback, please write to me directly: [email protected]

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