Top 5 Levi's Jeans to Cowboy Boots

Top 5 Levi’s Jeans that perfectly complement your cowboy boots

Every cowboy boot deserves a perfect pair of jeans to complement its style. Finding the right jeans for your cowboy boots goes beyond just fashion – comfort and practicality are key considerations. In this guide, I’ll share my personal experience with the top denim brand in the industry, helping you select the ideal pair of Levi’s that seamlessly suits your cowboy boots.

Move over peanut butter and jelly, Tom and Jerry, and pen and paper—cowboy boots and Levi’s jeans form one of the most impeccable duos.

Surprisingly, Levi’s jeans were initially designed with cowboys in consideration. Yes, you heard it right: the brand soared in the 1920s, gaining immense popularity among cowboys, railroad workers, and loggers.

Fast forward a century, and Levi’s remain the top choice for pairing with cowboy boots. It’s not only about the enduring iconic style; it’s also about the perfect fit, protection, and comfort you could ever desire.

Top 5 Levi’s Denims For Cowboy Boots

Levi’s 501 Original Fit Jeans

A timeless classic, the 501 Original Fit provides a straight leg and comfortable fit that complements cowboy boots effortlessly.

The spaciousness of the seat ensures that you can sit comfortably in a saddle for extended periods.

The leg has ample width to effortlessly slip over a pair of cowboy boots, avoiding any flared-out or bell-bottomed appearance.

What I love most is that there’s such a diverse range of styles and colors to choose from. It allows you to change up the appearance of your jeans without compromising on the cut or comfort.


  • A loose and relaxed fit, perfect for those who are built.
  • Durable denim holds up well over time, resisting quick fading, fraying, or scuffing.
  • Perfect for both workdays and weekends, providing comfort and convenience in any setting.
  • You can choose from a diverse array of styles.


  • Traditional Levi’s 501 jeans may lack the stretch found in some modern denim styles, potentially limiting flexibility and comfort for some individuals.
  • The rigid nature of the denim means there is often a break-in period required for the jeans to conform to the wearer’s body, which may initially feel less comfortable.
  • Levi’s 501 jeans are positioned at a relatively higher price point compared to some other denim brands, which may be a consideration for budget-conscious shoppers.


Levi’s Original 501s are my absolute favorite when I slip into my cowboy boots, but what’s even cooler is how seamlessly they pair with practically any type of footwear.

Not only are they super comfy, allowing my legs the freedom to move, but they’re also robust enough to endure the test of time. Knowing they’ll stick with me for years is a major win.

And the cherry on top? Since they’re one of Levi’s hottest picks, I can easily snag a pair at any local store or with just a few clicks online. It’s that dependable combo of style, comfort, and accessibility that keeps me coming back for more.

Levi’s Loose Fit 569 Jeans – Affordable and Fashionable

What I really appreciate about the Levi’s Loose Fit 569 Jeans is not just the price tag, but it’s definitely one of the things that stands out to me.

These jeans are not only amazingly budget-friendly compared to other options from Levi’s, but it’s their versatility that really draws me in.

Here’s the scoop: the fabric crafting these jeans is 99% cotton, which is your standard denim material, but there’s that extra 1% elastane, also known as Lycra, adding a touch of flexibility.

Including a touch of elastane in these jeans provides the right amount of stretch, allowing them to move and flex seamlessly as I navigate through my day. What’s great is that this added flexibility doesn’t sacrifice the durability of the jeans.

Not only are these jeans accommodating in the seat and thigh, but they also feature a straight leg that effortlessly glides over a pair of cowboy boots. The length is just perfect, showing off my beloved cowboy boots in all the right ways.


  • Affordable and long-lasting.
  • Including elastane in the fabric blend adds a great level of stretchiness, making them super flexible and versatile.
  • The straight leg cut is just ideal when you’re pairing your jeans with cowboy boots.
  • These jeans rest comfortably below the waist, giving off a laid-back vibe for a relaxed and easygoing appearance.
  • Can you believe it? The Loose Fit 569s have gathered a whopping 34,000 reviews and are still rocking a stellar 4.5-star rating. Now, that’s seriously impressive!
  • A lot of folks rave about how soft the fabric is, saying it feels even smoother against their skin compared to regular denim.


  • Due to their loose fit, these jeans may not be suitable for more formal or business casual occasions, limiting their versatility in certain settings.
  • These jeans aren’t the best for jobs in really hot places because the elastane they have can catch fire. So, they’re not a good choice for welders and some folks working in factories.
  • Just like many other Levi’s jeans, there seems to be a bit of a gamble when it comes to getting the right size. Some folks have voiced concerns about ordering two pairs of the same size simultaneously, only to end up with two different-sized pairs when they arrive.


Levi’s really hit the jackpot in the budget-friendly department with the Loose Fit 569 Jeans. These jeans stand out as some of the most versatile ones I’ve tried so far. The cut is super comfy, and the stretchable fabric makes them perfect for everything from riding and working to just kicking back and relaxing.

Levi’s 501 Shrink-to-fit Men’s Jeans: Value For Money

Levi’s Shrink-to-Fit Jeans have this real, timeless vibe. The raw denim gives off this cool mix of being tough and stylish at the same time, hitting that perfect balance between rugged and refined.

What I really enjoy about these specific 501s is that the more I throw them in the wash and wear them, the more the denim sort of hugs and conforms to the contours of my body.

The straight leg and comfy fit stay intact, but it’s like the jeans just cozy up and become even more tailored to my size with each wear.

After rocking these for just a year, they’ve got this incredible “lived-in” vibe that none of my other jeans even come close to.

Honestly, it’s hard to imagine getting better bang for my buck than this.


  • These raw denim jeans shape themselves around your body, making them feel like they were tailor-made just for you.
  • Stylish look, comfortable cut.
  • The straight-leg style is perfect for effortlessly wearing over boots.
  • They feel really comfy around my waist.
  • With more than 6,100 reviews and an impressive 4.4-star rating, it’s pretty clear that a ton of folks out there really like what Levi’s has nailed down with the 501 Shrink-to-Fit Men’s Jeans.
  • The jeans are available in a diverse range of washes, allowing you to select the one that suits your style preferences, whether you prefer a classic indigo or a more modern faded look.


  • Unlike pre-washed jeans, the Levi’s 501 Shrink-to-Fit requires the user to go through the shrinking process, which may be seen as an inconvenience for those who prefer ready-to-wear options.
  • When I got these initially, I was hoping for the same heavy-duty vibe as the Original 501s. While I’ve grown to like their more “light-duty” feel, they just don’t match up when it comes to the durability I require for work pants.


I could talk endlessly about how much I love my Levi’s 501 Shrink-to-Fit Men’s Jeans because they’re just so darn comfy. As time has passed, I’ve really grown fond of the well-worn, laid-back vibe they’ve developed. When it comes to their cost, dependability, and adaptability, I honestly think they’re a fantastic investment.

Top Pick for Bootcut Style: Levi’s 527 Slim Fit Bootcut

I usually go for work jeans with a bit more breathing space, but when I’m off the clock, I’m all about Levi’s slim fit. The sleek, trim cut just adds a touch of style that pairs perfectly with a polo, collared shirt, or my go-to leather jacket.

The Levi’s 527 Slim Fit Bootcut jeans give me the perfect fit I’m after, and they have just the right amount of flare at the pant leg to match up with my cowboy boots.

Even though they hug my waist and thighs a bit more snugly, the added elastane mixed with the cotton ensures they never feel too tight or constricting.

These are my trusty jeans, perfect for pairing with a stylish set of dress cowboy boots when heading out for a date night or catching up with friends at the nearby pub.


  • The inclusion of stretch fabric in the denim provides added comfort and flexibility, ensuring ease of movement throughout the day without sacrificing the desired slim fit.
  • Offers a contemporary and stylish silhouette that caters to those who prefer a slimmer fit without compromising the bootcut design.
  • Known for their durability, Levi’s jeans, including the 527 Slim Fit Bootcut, are crafted with high-quality materials and construction, ensuring longevity and resistance to wear.
  • Friendly on your bank account


  • Individuals with shorter legs may find that the length of the bootcut can be too long, requiring alterations for a proper fit, which could be considered an inconvenience.
  • The denim turned out to be thinner and more prone to tearing than I anticipated. These jeans aren’t the sturdiest ones in my collection, so I usually reserve them for social occasions rather than putting them to the test at work.


When it’s time to hit the town, I always reach for my Levi’s 527 Slim Fit Bootcut jeans. They’re comfy, got that cool style, and light enough to bust a move on the dance floor all night long. These Levi’s are the dream pair – exactly what I need for slim-fit, bootcut perfection.

Ideal for Movement: Levi’s 511 Slim Fit Jeans

I always go for the Levi’s 511 Slim Fit Jeans when I need to keep up with the hustle and bustle of fast-paced days.

The denim here has a cool twist – it’s got 2% elastane mixed with the cotton, making it surprisingly stretchy.

I’ve put these jeans through the wringer, playing soccer, racing through Costco before it shuts down, and even doing some flooring work. They’re like the superhero of pants, all thanks to that flexy fabric and the sleek cut.

Now, the leg is a tad slimmer than my ideal fit. Wrestling them down over my work boots takes a bit of effort, and you can still catch a glimpse of the boot’s outline peeking through.

But when it comes to dressing up with boots, that slim fit and slender legs create a super sleek and stylish vibe that you just can’t achieve with the wider bootcut or relaxed fit jeans.

Even better, these jeans come in Big and Tall sizes, making them an ideal choice for anyone standing above 6 feet.


  • The Levi’s 511 Slim Fit Jeans offer a contemporary and stylish silhouette, catering to individuals who prefer a more modern, slim-cut look.
  • With a slim fit that isn’t overly restrictive, these jeans are versatile and can be easily paired with various tops and footwear, making them suitable for both casual and semi-dressy occasions.
  • The addition of elastane to the fabric ensures these jeans are super flexible and easy to move in.
  • Available in a wide variety of washes.


  • These jeans have a slim leg that might not pair well with wide-mouthed cowboy boots.
  • Unfortunately, similar to some of Levi’s more recent styles, the 511s feature a thinner fabric that doesn’t quite stand up to the rigors of everyday work.


The Levi’s 511 Slim Fit Jeans are my go-to for summer vibes—they’re so light and comfy, plus the fabric’s got this amazing flexibility, thanks to those synthetic fibers. Perfect for throwing on with my favorite dress boots when I’m heading out for a night on the town.

Also read: 7 Men’s Western Outfits For A Country Concert

3 Tips To Perfectly Style Cowboy Boots With Jeans

Choose the perfect cut to match your cowboy boots.

Cowboy boots usually widen at the top, so you’ll want jeans with legs spacious enough to comfortably cover and hide the boot tops.

For a real cowboy vibe, the best jeans to rock with your boots are either straight-leg or boot-cut.

Yet, certain slim-fit jeans boast a leg width generous enough to cover your cowboy boots entirely—or, at the very least, match well with a more streamlined and less flared dress cowboy boot style.

Pick the Right Fit (and Length)

How they fit will depend on your body shape.

  • Guys who have a slimmer physique can rock straight-fit and low-rise jeans, giving their legs some definition and showcasing those sleek muscles.
  • Guys with broader shoulders and a narrower waist should opt for straight-fit jeans. This style helps maintain a balanced look, preventing the legs from appearing too thick for the hips and waist.
  • For guys with a bit more around the midsection, rocking high-rise, straight-cut, or relaxed-fit jeans is the way to go. These styles not only define the lower body but also work like a charm to keep that midsection on the down-low.
  • If you’re a guy with broader hips and slimmer shoulders, it’s a good idea to go for jeans with a loose, straight-fit, or relaxed-fit style. This choice helps create a more balanced look by complementing your proportions.

When it comes to wearing cowboy boots, don’t forget about the length factor. Those boots’ heels, usually ranging between 1 and 2 inches, give you a little extra height. That means your regular jeans might come up a tad short.

For instance, if you usually go for a 32-inch inseam when rocking sneakers, you would have to level up to a 34-inch insean to get that perfect fit.

Go For A Darker Wash

Levi’s in medium to dark shades simply rock the cowboy boots look, no doubt about it.

Lighter jeans, on the other hand, go great with sneakers, trainers, slip-ons, and casual vibes.

But when it comes to standing up to the ruggedness of leather cowboy boots, you need that darker hue.

Final Thoughts!

Let me emphasize the importance of not just any pair of jeans, but finding that perfect match – the one that ticks all the boxes.

The right pair of jeans becomes the cornerstone of your style, seamlessly complementing your boots, shirt, and jacket. It needs to be tough enough to handle the demands of your daily grind and busy life, while ensuring comfort that lasts all day, no matter what activities fill your schedule.

After putting numerous pairs to the test, I can confidently say that Levis Original 501s take the crown as the ultimate jeans for pairing with boots. They’re not just durable and reliable; they provide ample room for easy movement, whether you’re riding, ranching, or working.

Looking for a budget-friendly option without sacrificing versatility? The Levi’s Loose Fit 569 Jeans fit the bill surprisingly well. And if you’re aiming for the best value for your money, the Levi’s 501 Shrink-to-fit Men’s Jeans are my go-to. They mold to my frame over time, delivering that delightful “lived-in” feel with each wear.

The Levi’s 527 Slim Fit Bootcut finds that sweet spot between a trendy slim fit and legs that give enough room for my boots to slide right in. These aren’t just my top choice for bootcut jeans from Levi’s; they snag the second spot overall for pairing with boots.

And when it comes to keeping up with a busy day, nothing beats the freedom and flexibility of Levi’s 511 Slim Fit Jeans.

How To Wear Cowboy Boots With A Business Casual Outfit


Should I tuck my jeans into cowboy boots?

Men should only tuck their jeans into their cowboy boots when it’s really needed, like when you’re trying to keep your jeans clean and mud-free while working on your ranch or farm. In all other situations, jeans are meant to be worn over cowboy boots.

Which Levi’s jeans do cowboys mostly wear?

Levi’s 501s hit the spotlight way back in the 1930s, earning massive popularity because they were featured in those classic early Western movies. These jeans have a rich history, dating back 150 years, making them Levi’s oldest denim style. For almost a century, they’ve been the go-to iconic look for cowboys, etching their signature style into Western culture.

When did people start wearing Levi’s jeans?

In the beginning, Levi’s were mainly rocked by farmers, gold miners, and lumberjacks.

But as we rolled into the late 1890s and early 1900s, cowboys were ditching their regular pants – you know, those leather-lined “California foxed pants,” woolen ones, and corduroys – and hopping on the denim train, rocking those Levi’s.

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