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Wearing Cowboy Boots with Jeans: A Mans’ Guide

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I plan to go to the horse races this weekend with my lawyer friend. He owns some cool cowboy boots he’s never worn and isn’t sure what type of jeans to wear with them or if he should tuck them in or wear them outside of his boots. Here’s the advice I gave him concerning how to wear cowboy boots with jeans:

Wear your jeans over your cowboy boots not tucked in, make sure the back of your jeans cover your boot heel but don’t reach the ground, and your jeans should be form-fitting in the upper legs. The best-looking jeans to wear with cowboy boots are Wranglers.

Looking for men’s jeans to wear with your new cowboy boots but don’t know how to choose the right ones? Want to know the criteria for selecting jeans to pair with cowboy boots? Better still: want to know which are the best men’s cowboy boots jeans available in the market? 

Then join me today as I walk you through selecting the right pair of men’s jeans designed primarily for wearing those stylish cowboy boots.

Picture of cowboy boots with jeans.

In this guide, I cover:

  • Do guys wear cowboy boots over jeans?
  • Can you wear straight jeans or skinny jeans with cowboy boots?
  • 5 Best jeans for cowboy boots
  • And more..

Do Guys Wear Cowboy Boots Over Jeans?

Please don’t wear your cowboy boots outside of your jeans unless you’re trying to keep them clean when working. Women look good with jeans tucked into their cowboy boots, but 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, it is cheaper to wash boots than buy new jeans!).

Some cowboys wear their cowboy boots over their jeans to prevent them from 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 having to worry about the jeans getting tangled.

So, to answer the question: Do guys wear cowboy boots over Jeans? For fashion, no. But, for work or riding, yes, 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. In fact, 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, which are 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.

Also, read Best Bootcut Jeans for Women.

Picture of me wearing Tecovas cowboy boots with jeans.
Tecovas boots

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’d pull the jeans around the ankles to create the stacked effect).

But if you wear regular bootcut jeans, then ensure that 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!

Picture of tecovas boots.

Best Jeans for Cowboy boots for Men – 2022 Top 5 Picks

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

Wranglers makes authentic cowboy jeans, and the brand has 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 own several pairs in my wardrobe. 

The cowboy cut 936 slim-fit jeans from Wrangler fit snugly at the waist and make 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 pair of cowboy boots without showing the shaft too much when you ride.

It is no wonder that Wrangler is the official partner of ProRodeo Competition -their jeans are made for authentic cowboys. Even champions choose these jeans as they fit comfortably over cowboy boots.

You will love the all-cotton construction which keeps things breathable and sweat-free. The pair is also equipped with several pockets so you can keep your keys, phone, and other must-have items when riding or working on the ranch.

Features

  • Available in 10 awesome 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 horse riding
  • 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 returns 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 as well. 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 jean for Rodeos, and it fits perfectly over cowboy boots. Moreover, it is available in so many sizes and colors that you’re sure to 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 their name by offering durable yet comfortable cowboy boots; however, they also make great jeans. I love the over-the-boot silhouette of these bootcut jeans from ARIAT – another favorite brand of mine, Ariat M4 boot cut jeans also feature a stackable design that comes over your boots and is sure to draw eyes to your fashionable cowboy boots.

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 pocket, 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 flex and comfort.

Also, Levi’s jeans use way less water compared to 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 compared to 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 who carry knives or sharp tools in their pockets.

#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. 

If you do not mind the high price tag, these are the best premium jeans to opt for.

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

  • Many imitation/fake Lucky Brand jeans are available in the market. Do ensure you are buying the real thing.

How it compares

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

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

Picture of me wearing cowboy boots with jeans.
Ariat Amos boots

FAQs

How to wear jeans with cowboy boots?

The experts from ARIAT recommend selecting jeans with a proper fit. They can be dark to medium dark-wash colors. They also recommend boot cut/relaxed fit/regular straight leg jeans paired with cowboy boots.

Why do some cowboys wear their pants in their boots?

Cowboys often tuck their pants in their boots to prevent them from getting dirty and torn while riding on trails or working in the stalls.

What jeans do real cowboys wear?

Most rodeo and working cowboys wear Wranglers, but these days, many of the younger cowboys are wearing other top denim brands like Levy, Ariat, and Lucky Brand jeans. In the past, authentic cowboy jeans were thicker than usual jeans to keep the rodeo heroes safe and comfortable. The thicker materials enhanced the jeans’ durability and prevented wear and tear.

Why do cowboys wear tight/stiff jeans?

Cowboys participate in rodeos and work around bulls, horses, and other animals. The denim material is thick, tough, and durable and prevents rips and tears in case of falls. The tightness of the pants also prevents billowing or flapping, which can spook a horse or get caught up in the rigging.

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, there are many great choices for men when it comes to 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 selecting men’s jeans to wear 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, avoiding 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!