Wearing Cowboy Boots with Jeans: A Man’s Guide

Last updated: November 21, 2023

By: Miles HenryFact Checked

When pairing cowboy boots with jeans, the key is to ensure a comfortable yet stylish fit. Your jeans should sit over your cowboy boots, not tucked in. The ideal fit involves jeans that cover the back of the boot heel without dragging on the ground and are snug around the upper legs. Wrangler jeans are the top choice for a classic cowboy look due to their fit and durability.

In this article, I’ll cover the specifics of selecting the right jeans to complement your cowboy boots. Whether heading to the horse races or any casual event, understanding the nuances of cut, length, and style will elevate your outfit. I’ll guide you through the process, helping you to make a fashion statement with this timeless combination.

Should You Wear Cowboy Boots Over Jeans?

Please don’t wear your cowboy boots outside your jeans unless you’re trying to keep them clean when working. Women look good with jeans tucked into their cowboy boots, but for men, not so much – it simply isn’t fashionable.

However, if your job entails working in the barn or ranches, mucking stalls, or wading through mud, tuck your jeans into your boots if you feel like it; that way, you can protect your jeans’ legs from dirt and tears. (After all, washing boots is cheaper than buying new jeans!).

I took my jeans in when working in wet areas, but not around the horse barn because I always end up with shavings in my boots when I have my jeans tucked in.

Some cowboys wear cowboy boots over their jeans to avoid getting caught in the branches and thorns. Another benefit of tucking jeans into the boots is that you can easily and comfortably place your legs in stirrups while riding without worrying about the jeans getting tangled.

I’ve never had a problem with my jeans getting tangled, and I always ride with them on the outside of my boots.

So, to answer the question: Do guys wear cowboy boots over Jeans? For fashion, no. But, for work or riding, you can wear cowboy boots over jeans for practical reasons.

Can You Wear Straight Jeans or Skinny Jeans With Cowboy Boots?

When wearing cowboy boots with jeans, men shouldn’t wear skinny jeans. Women can wear skinny jeans with cowboy boots. But men shouldn’t; it’s a fashion faux pas. Real cowboys don’t wear skinny jeans. 

When it comes to finding the right pair of jeans for men to wear with cowboy boots, opt for the bootcut style in a relaxed fit or regular fit; you can also go in for jeans flared below the knees but tight above them. 

Some modern cowboys also wear stacked or stackable jeans, cut longer than normal and create a stacked effect at the ankles to draw attention to the boots.

However, men should not wear skinny jeans with cowboy boots and may leave that pairing to the ladies. Men don’t need to get fancy; buy yourself a nice-looking, comfortable-fitting pair of bootcut jeans.

Also, read Best Bootcut Jeans for Women.

How Long Should Your Jeans Be With Cowboy Boots?

For men, ideally, the jeans should be slightly longer than normal when wearing them with cowboy boots. The jeans should cover the heel without dragging to the ground (unless you go for the stacked design. Even then, you will pull the jeans around the ankles to create the stacked effect).

But if you wear regular bootcut jeans, ensure they do not end at the ankle but give an allowance of 1/3rd to 1/4th of the instep. This will prevent showing the cowboy boots too much. 

This is even more important when you ride as your jeans will get pulled up slightly, but the extra length of the jeans will prevent the boot’s shaft from being over-exposed. And that is how it should be!

Below is a good YouTube video on wearing jeans with cowboy boots.

Best men’s Jeans for wearing with cowboy boots-2022 Top 5 Picks

#1. Winner: Wrangler Men’s Cowboy Cut Original Jean

Wranglers make authentic cowboy jeans, which have been around for nearly seven decades. It is no wonder that they have maintained their position as the global leader in Western-inspired American wear. I have been a ‘Wrangler man’ for years and have several pairs. 

The cowboy-cut original jeans from Wrangler fit snugly at the waist, making your legs look long and lean. At the same time, they are made for the working man and do not look unprofessional, baggy, or saggy.

They are ideal for showing off your new cowboy boots without showing the shaft too much when you ride. Note: If you’re not used to wearing original Wranglers, there are a few things you should be aware of:

First, they are stiff when you first get them. Second, the denim is heavier than most jeans, and finally, they run a bit small. For example, I typically wear size 32 in most pants, but I fit 33 in these Wranglers.

It is no wonder that Wrangler is the official partner of the ProRodeo Competition -their jeans are made for authentic cowboys. Champion rodeo cowboys choose Wrangler jeans because they are comfortable, durable, and designed for riding horses; plus, they fit comfortably over cowboy boots.

You will love the all-cotton construction, which keeps things breathable and sweat-free. They also have several pockets to keep your keys, phone, and other must-have items when riding or working on the ranch.

Features

• Available in 10 fantastic colors like Indigo, bleach, shadow black, stonewash, etc.
• More than 40 sizes!
• 100% Cotton
• 5 pocket-design
• 7 belt loops 
• Constructed with a slim fit through the thigh and seat.
• Iconic Wrangler patch with W back pocket

Benefits

• Excellent to wear with cowboy boots
• Multiple belt loops prevent the jeans from sagging when horseriding
• Multiple sizes and color options

Drawbacks

• For some users, the regular size did not fit. It ran a bit small. 

Expert Tips

• I suggest ordering 3-4 of these jeans in a couple of sizes close to your usual size. This way, you can try the different pairs comfortably in your home and return the ones that do not fit well.

How it compares

Many people compare the Wrangler 936 Slim-fit with Levi’s 514 cowboy jeans. However, the Wrangler wins in several aspects: it is cheaper, and the design is slimmer. Moreover, the material is a lot more durable.

Many cowboys (including yours truly) have blown their Levis’ jeans at the knees, but not the Wrangler. This pair of jeans has withstood the test of time and is built to last. Wrangler Slim Fit Jean is also the official cowboy jeans for Rodeos, and it fits perfectly over cowboy boots. Moreover, it is available in so many sizes and colors that you will indeed find something you love. I love that it has multiple belt loops that prevent the briefs from showing. Need I say more?

Also Read: 10 Most Comfortable Western Cowboy Boots for Flat Feet 

#2. Best Bootcut Low Rise Cowboy Jeans – Ariat M4 Relaxed Fit Men’s Denim

Ariat made its name by offering durable yet comfortable cowboy boots, but they also make great jeans. I love the over-the-boot silhouette of these bootcut jeans from ARIAT – another favorite style of mine, Ariat M4 bootcut jeans that also feature a stackable design that comes over your boots and is sure to draw eyes to your fashionable cowboy boots.

Note: You can buy these jeans directly from Ariat and often save a few dollars.

Here are some of its great features:

Features

• Premium blend of cotton plus denim
• Stackable design boot-cut style with low-rise waist and relaxed fit
• Available in 9 colors and nearly 32 sizes
• Heavy-duty zippers, coin pockets, and anchored belt loops
• Leather accents

Benefits

• True to size
• Value for money

Drawbacks

• Prone to shrinking and fading after wash

Expert Tips

• These jeans are not FR or flame-resistant, as indicated. The brand does make FR jeans – in case you want them for work.

How they compare

Ariat M4 jeans are reasonably priced, durable, and perfect for ranch work. The bootcut style with a stackable design is ideal for showing off your cowboy boots. There are plenty of choices available too as far as the colors and sizes are concerned.

Find Out: What Are Real Cowbout Boots – Complete Guide

#3. Best Slimming Jeans for Men Cowboy Boots: Levi’s Men’s 527 Slim Bootcut Fit Jeans

Levi’s is another American classic brand, so we cannot really talk about jeans without talking about Levi’s. These slimming jeans fit well around the legs, thighs, and waist. They contain unique material with advanced stretch technology that offers flexibility and comfort.

Also, Levi’s jeans use less water than many other denim brands, so it is a great choice for environment-conscious people.

Features

• 15% organic cotton + 84% Ecoease cotton + 1% Elastane
• Boot cut style
• Available in 28 colors and more than 30 sizes

Benefits

• Stretchy
• Stylish
• Slimming
• Comfortable

Drawbacks

• Size issues

Expert Tips

The jeans shrink after washing, so buy a size up if needed.

How they compare

Levi’s brand is a reputed name when it comes to denim wear. However, off-late, there have been some size and quality inconsistencies. Also, most Levi’s products are made in Asian countries. 

The brand’s aficionados have complained about thinner material than their earlier products. Some even felt that the regular size did not fit them well (despite no significant weight changes). However, others were very impressed with Levi’s slim-fit jeans fit, style, and comfort. Their style is also ideal for pairing with cowboy boots.

Also Read: Best Cowboy Boots for Kids

#4. Best Budget Buy: Wrangler Authentics Relaxed Fit Men’s Boot Cut Jeans

Wrangler Authentics is also an offering of the Wrangler brand. These boot-cut jeans have received thousands of positive reviews thanks to their versatility, comfort, and timeless silhouette. The price is super-attractive too.

Features

• Made with spandex (1%), cotton (78%), and polyester (21%)
• 5-pocket design, boot cut style, relaxed seat, and thigh, and sits at natural waistline.
• Available in 8 colors and over 20 sizes

Benefits

• Affordable
• Comfortable
• Soft texture
• Versatile

Drawbacks

• A few users found them too baggy and shapeless.

Expert Tips

• All colors are fantastic, but most users loved the ‘riptide’ shade in these jeans..

How they compare

Wrangler Authentics relaxed-fit boot-cut jeans are ideal for pairing with cowboy boots. Their price is very attractive and ideal for those on a budget. The material is soft and ultra-comfortable – great for riding on hot days. However, it is a bit thin and may not suit people carrying knives or sharp tools.

#5. Best Premium Bootcut Jeans: Lucky Brand Men’s 367 Vintage Bootcut Jean

The Vintage 367 from Lucky Brand has a classic bootcut, easy mid-rise, and a relaxed fit. The leg opening of 20 1/4th inches makes it ideal for pairing with cowboy boots. 

These are the best premium jeans if you do not mind the high price tag.

Features

• Made with cotton (98%) and Spandex (2%)
• Zipper closure
• 5 pocket

Benefits

• Excellent fit
• Classic style
• Durable

Drawbacks

• Some men found it too stretchy

Expert Tips

• There are many imitation/fake Lucky Brand jeans available in the market; don’t be fooled; ensure you are buying the real thing.

How it compares

The Vintage 367 from Lucky Brand features a classic boot cut style to help you show off those new cowboy boots. On the downside, their price is slightly higher than our winning entry. 

Also, read Cheap Cowboy Boots – Stylish, Durable, and Comfortable.

FAQs

Key Takeaways – Men’s Cowboy Boots with Jeans

Cowboy boots and jeans are a stylish and functional combination when riding or working on ranches. Today, men have many great choices when selecting the best jeans to wear with cowboy boots. You can opt for brands like ARIAT, Wrangler, and Levi’s; you simply can’t go wrong with them.

When wearing men’s jeans with cowboy boots, choose a bootcut style, relaxed fit, or regular leg. Avoid skinny jeans (although the combination works well for women). When working, you can tuck the jeans inside your boots, but for regular wear, avoid doing so as it is considered a fashion faux pas.

I hope this guide helps you choose the best pair of jeans to show off those cowboy boots in style!

FAQs