Best Levi’s for Cowboy Boots: Top 5 Pairs in The Ultimate Style Guide for Men

Best Levi’s for Cowboy Boots and How to Choose the Pair That is Right for You

Levi’s is a classic brand and provides you numerous options to pair with your cowboy boots. They have several different styles and cuts that will fit with cowboy boots. Levi’s and boots go well together and will help outfit you in comfort and style. As you search for the best Levi’s for cowboy boots you will find different pairs with cuts to complement different body types. Knowing which ones will work best for you will help ensure that you find a pair that fits both your legs and your boots.

In this writeup, we will use some of our own personal experience as well as what we’ve found online to zoom in on some of the top Levi’s options that look and fit great with cowboy boots. This will include classics like the Levi’s Men’s 501 to more contemporary choices such as the Levi’s Men’s 541. In finding pairs to present to you we will take into account the various important factors – such as boot shaft height, leg opening size, and overall style to ensure that you end up with a well-coordinated and stylish look.

As you read through and explore the following recommendations, it is important to remember that your own personal preferences will play perhaps the most significant role in determining what will be your ideal Levi to wear with cowboy boots. Keep in mind your own tastes in jeans as well as the occasions you plan to be wearing your cowboy boots to. This approach will guide you to select the right Levi’s to wear with your cowboy boots.

History of Levi’s and Cowboy Boots

Levi’s started off in San Francisco after being founded by Levi Strauss in 1853. He had just moved from New York City where he had worked with his brothers in the dry goods business. Opening during the gold rush he started with a dry goods business. Quickly moving into other areas to support customers in 1873 Levi Strass received a US patent that allowed them to create the work pants that would become the blue jeans we know and love today.

The popularity of cowboy boots continued to grow and over time Levi’s blue jeans became a natural pairing for cowboy boots.

The original Levi jeans weren’t made specifically for cowboy boots, but the fit was a natural pairing. With the jeans sitting comfortably at the waist while maintaining a straight leg all the way down, it was a pairing that just made sense with boots.

As we move into the modern era Levi’s now offers multiple styles and cuts of jeans that pair well with cowboy boots. Our top 5 selections for men’s Levi’s jeans for cowboy boots are:

• Levi’s 501 – The classic and original cut
• Levi’s 505 – regular fit with a bit more space in the thigh area
• Levi’s 541 – athletic fit, straight leg, slightly slimmer look, but extra room in seat and thigh
• Levi’s 513 – Slim fit, straight leg, mid-rise, sits just below waist,
• Levi’s 559 – relaxed fit, straight leg, roomy seat and thigh, roomiest pair on this list

We will go into a more detailed description further down.

As you can see from a brief look at the history of Levi’s and cowboy boots, this iconic combination has stood and will continue to withstand the test of time. You can expect to see the brand evolve to maintain relevance and appeal over time as needed.

Best Levi’s Styles for Cowboy Boots

Bootcut Jeans

While we don’t include any specifically bootcut jeans on our top 5 list that doesn’t meant they’re not a good choice. Personal preference is for a smaller leg opening in our list. However, if you want a bit bigger leg opening and make sure you lower your chances of boot printing then a bootcut fit is for you.

Levi’s 527 bootcut jeans will give you a classic and versatile option to pair with your cowboy boots. These jeans are designed to sit below the waist and feature a more slim fit through the seat and thigh. The bootcut leg opening is larger than most straight leg jeans by a couple of inches and works out perfectly to accommodate your cowboy boots while still creating a sleek silhouette.

Straight Leg Jeans

Straight leg jeans will appeal to those looking for a more traditional fit. All of our top 5 list of best Levi’s for cowboy boots are straight leg pairs. Straight leg jeans will give you a comfortable and classic option to pair with cowboy boots. The straight leg will give you enough room for boots to fit under.

Slim Fit Jeans

Slim fit jeans will not always work well with cowboy boots. If you get a straight leg pair with a slim fit in the waist, hips, and thigh then you can be ok, but you don’t really want to go the full skinny jean treatment with cowboy boots. If you do then you are setting yourself up for some serious printing with the tight fit around the ankles and most people don’t find that look to be appealing. The 513 with a straight leg, but slim fit is an example of a pair that fits this category. 

How to Choose the Right Levi’s Size and Fit

While considering the right Levi’s jeans to wear with your cowboy boots here are a few items to keep in mind to ensure you get the right style and fit.

How long should your Levi’s be when wearing cowboy boots?

Consider if you want to wear your jeans without much break in them or if you want more of what is called “stack” which is where the jeans stack on the boots for a couple inches. If you like the stack look then you will probably want to consider an inseam from between 2 and 4 inches longer than your normal inseam. If you don’t want or like the stack look then sticking with your normal inseam will probably work for you.

Understand the different fits

Are you looking for a big boot opening in the leg, do you want a more athletic fit or a more slim fit – these are the things to consider between the styles of Levi’s.

Keep the leg opening in mind

Bootcut style is the largest opening, but straight cut style accommodates all but the widest shaft cowboy boots. Slim cut or taper legs will take you into a concerning area where your jeans may clearly show through your boots – often known as printing. While some printing is normal and understood, extreme printing is considered unfashionable and unappealing by most.

Top 5 Best Levi’s for Cowboy Boots

Levi’s 501 with cowboy boots

• The original classic blue jean this style will give you everything you need. With a straight leg and classic fit and a leg opening that accommodates boots nicely you can’t go wrong with this choice.

Levi’s 505 with cowboy boots

• A close runner up and another long time favorite this cut is a straight fit jean with a little more space in the seat and thigh area to give a little extra space. But not so much space that these go into the category of dad jeans!

Levi’s 541 with cowboy boots

• The 541 is a cut that gives you an athletic fit which means they give you a bit more room in the seat and thigh to accommodate more muscle, but still have a nice silhouette. With a straight leg they work great with cowboy boots.

Levi’s 513 with cowboy boots

• This more modern cut incorporating a more slim fit is a nice pair of jeans, but not for the bigger guys. You will want to be both in shape and thin to best rock this pair. It still has the straight leg which makes it a good choice for cowboy boots while giving you a slimmer fit up high.

Levi’s 559 with cowboy boots

• The 559 is a relaxed, straight fit jean and is perfect for the bigger guy who wants a bit more room in the seat or thigh, but still wants something not quite dad jeans like. This is the roomiest pair on this list and has a larger leg opening than most which makes it a good choice for cowboy boots.

Wrapping It All Up

Ok, we are at the end. What did we learn? First up, there are more than one pair of Levi’s jeans to wear with your cowboy boots that can be a good choice. Second, when reviewing the options make sure to focus on comfort, fit, and your personal style. Third and final, have fun! Your jeans and your cowboy boots are part of your own style. Make it yours and own it.

FAQ for Best Levi’s for Cowboy Boots

What are some of the best Levi’s jeans to wear with cowboy boots?

Our top 5 list here are the Levi’s 501, 505, 541, 513, and 559.

Can I wear skinny jeans with cowboy boots?

Skinny jeans do not usually work the best to wear with cowboy boots. Their tight leg opening and slim taper will leave your boots printing extensively which isn’t considered an ideal look.

Do Levi’s 501 jeans fit over cowboy boots?

Yes, they fit over most pair unless you have a pair with a very wide shaft. Wearing 501’s with cowboy boots is a classic and iconic choice that looks great.

Are Levi 541’s good with cowboy boots?

Yes,  Levi’s 541 jeans are good with cowboy boots. These athletic fit jeans are a great choice and in the top 3 for our rankings.

Where can I purchase Levi’s jeans suitable for wearing with cowboy boots?

Levi’s jeans are widely available and can be found in Levi’s retail stores, their official online store, and many other online and in person clothing and department stores.

Are Levi’s jeans durable enough for rodeo use or other heavy-duty activities?

Levi’s jeans in general, and especially their rigid denim varieties, are generally regarded for their durability and quality.

Is there a particular color of Levi’s jeans that pairs best with cowboy boots?

While choosing one “best” color of jeans is entirely subjective and depends on your personal style, picking a traditional dark blue or dark wash color of jeans will often best complement the look of cowboy boots. Depending on the color of your boot and where you are wearing them you can also (and should) choose from some of their jeans in black, grey, and a variety of other colors.

Can Levi’s jeans be worn with cowboy boots for a dressier occasion?

Absolutely! When going to a dressier occasion you should try out pairing a darker wash of Levi’s jeans with a clean and sharp looking pair of cowboy boots. Complete this combination with a nice button-down shirt and a more casual blazer to really elevate your look. This last look can definitely be a good choice if you are wearing your cowboy boots to an interview.

You can watch a Youtube video that is based on a summary of this article by going here: https://youtu.be/UUEeUyUKj3E