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Step aside peanut butter and jelly, Tom and Jerry, and pen and paper—cowboy boots and Levi‘s jeans are as close to the perfect pairing as it gets.
In fact, did you know that Levi’s were originally constructed with cowboys in mind?
That’s right: the brand boomed hugely in the 1920s because of its popularity among cowboys, railroad workers, and loggers.
Flash forward 100 years, and Levi’s are still the best pants you can wear with cowboy boots. It’s not just an iconic style pairing; it’s also the ideal fit, protection, and comfort you could ask for.
How Did I Come Up With My List?
My first pair of jeans were Levi’s, and my first boots were cowboy boots. Enough said?
I’ve been a Levi’s guy for nearly three decades. They’re my go-to brand for jeans, my tried-and-true, ride-or-die.
Their durability, fit, and sharp look make them my top pick whether I’m lounging on my day off, heading out for a night on the town, or saddling up for a ride.
And here in central British Columbia, the only thing that properly completes the “Canadian tuxedo” (aka, denim pants and jacket) is a good pair of cowboy boots.
It’s safe to say I’ve invested hundreds of hours into researching and personally testing Levi’s jeans over the years. I’ve got drawers full of Levi’s—from “dress-up” jeans to work jeans to weekend jeans.
I’ve winnowed down the list of all the best Levi’s offerings to bring you the five pairs I’ve found wear best with a pair of cowboy boots.
The Best Levi’s Jeans to Wear With Cowboy Boots, for Work or Style
Best Overall: Levis Original 501s
After years of research, I have yet to find a pair of Levi’s jeans that wears as well as the Original 501s.
These Levi’s have a relaxed fit that makes it easy for me to move easily. Whether I’m swinging in and out of a saddle, digging post holes, or running errands, I’ve got total freedom of movement.
The roominess of the seat also makes them comfortable sitting in a saddle for long hours.
The leg is wide enough to fit over a pair of cowboy boots without looking like they’re flared out or bell-bottomed.
I’ve tested the high-quality denim and found that it holds up well to every manner of work. From job sites to barn building to DIY fix-its around my property, the Original 501s are built to last.
Best of all, the wide assortment of styles and colorways available means I can switch out the look of my jeans without changing the cut or comfort.
What I Like
Loose, relaxed fit great for a heavier-built guy like me.
Sturdy denim won’t fade quickly, fray, or scuff.
Comfortable and convenient for work and weekends both.
Available in a wide range of styles.
What I Don’t Like
The price tag is significantly higher than any other jeans on this list—and almost every other pair of jeans I’ve worn to date. They’re not a splurge, but their quality is undeniable.
What Other Reviewers Say
Reviewers appreciate the “no-nonsense” construction and durability of the Original 501s. Their all-purpose look and utilitarian design also score high marks among reviewers.
A few reviewers highlight the lower quality of the denim, claiming “they aren’t what they used to be.”
However, there’s no argument that they’re the ideal pair of Levi’s to pair with cowboy boots no matter what you’re doing.
The Verdict
Levi’s Original 501s are my go-to when I’m wearing cowboy boots, but I’ve come to love how well they match with just about any style of shoes.
They’re comfortable, give my legs room to move, and tough enough that I can trust them to last me for years. Best of all, because they’re one of Levi’s most popular offerings, I can always find them in stores or online.
Possibly the most well-known jeans around, the 501s are the quintessential 'original' Levi's. It's a style that's endured since known since 1873, featuring the original straight fit for an All-American look with a button fly and 5 Pocket Styling.
Best on a Budget: Levi’s Loose Fit 569 Jeans
The price tag is just one of the things I like about the Levi’s Loose Fit 569 Jeans.
Don’t get me wrong: they’re wonderfully affordable compared to most of Levi’s other offerings.
However, it’s their versatility that keeps me coming back.
You see, the denim used to build these jeans are 99% cotton (standard for jeans) but 1% elastane (aka Lycra).
The addition of that small amount of elastane gives them just enough stretch that they move and flex with me as I go about my day, but without compromising the jeans’ durability.
The jeans are also roomy in the seat and thigh, with a straight leg that slides nicely over a pair of cowboy boots and hangs down to just the right length to show off my cowboy boots.
What I Like
Budget-friendly yet long-lasting.
The addition of elastane makes them nicely stretchy and highly versatile.
Straight leg is perfect for wearing with cowboy boots.
The jeans sit below the waist for a more relaxed look and feel.
What I Don’t Like
I can’t use these jeans for work in high heat environments because the elastane will catch on fire. That makes them unsuitable for welders and some factory workers.
What Other Reviewers Say
The Loose Fit 569s have amassed a mind-boggling 34,000 reviews and still have a 4.5-star rating. Impressive, to say the least.
Reviewers rave about their cut, comfort, and quality. Many highlight the softness of the fabric and claim it feels smoother against their skin than regular denim.
As with a lot of Levi’s jeans, quality control on sizing in particular seems to be a bit hit-or-miss. Customers complain about ordering two pairs of the same size at the same time, only to receive two different-sized pairs on delivery.
The Verdict
Levi’s strikes budget-friendly gold with the Loose Fit 569 Jeans. They’re among the most versatile jeans I’ve tested to date, with a comfortable cut and stretchable fabric that is wonderful for riding, working, or relaxing.
Levi’s strikes budget-friendly gold with the Loose Fit 569 Jeans. They’re among the most versatile jeans I’ve tested to date, with a comfortable cut and stretchable fabric that is wonderful for riding, working, or relaxing.
Great Value: Levi’s 501 Shrink-to-fit Men’s Jeans
There’s something authentic and classic about Levi’s Shrink-to-Fit Jeans. The raw denim has a look that strikes a nice balance between rough and rugged and stylish.
What I love about this particular pair of 501s is that the more I wash and wear them, the more the denim fibers compress and mold to the shape of my body.
The straight leg and comfortable fit is never compromised, but it feels like the jeans become more and more “made to size” with every wear.
After just a year of wearing these, they’ve developed a marvelous “lived-in” feel that none of my other jeans can match.
I can’t think of better value for my money than that.
What I Like
The raw denim molds to your body until they feel like they’re made for you.
Stylish look, comfortable cut.
Straight leg is ideal for wearing over boots.
They sit very comfortably on my waist.
What I Don’t Like
When I first bought them, I expected them to be as heavy-duty as the Original 501s. I’ve come to appreciate their “light-duty” feel, but they don’t deliver the same durability I need in work pants.
What Other Reviewers Say
With over 6,100 reviews and a 4.4-star rating, it’s safe to say a lot of reviewers appreciate what Levi’s has done right with the 501 Shrink-to-fit Men’s Jeans.
A few users had the same complaint I did, that the jeans weren’t quite as heavy-duty as they wanted and weren’t tough enough for work use.
However, the majority of real-life buyers are satisfied with these 501s, praising their adaptable comfort, easy breaking-in process, and versatile fit.
Reviewers also appreciated the wide range of colorways available.
The Verdict
I’ll sing the praises of my Levi’s 501 Shrink-to-fit Men’s Jeans all day long because they are comfortable. Over time, I’ve fallen in love with the lived-in and light-duty feel of these jeans. Their price tag, reliability, and versatility make them an excellent investment in my opinion.
I’ll sing the praises of my Levi’s 501 Shrink-to-fit Men’s Jeans all day long because they're so comfortable. I have a lot of love for the lived-in and light-duty feel of these jeans. Their price tag, reliability, and versatility make them an excellent investment, in my opinion.
Best Bootcut: Levi’s 527 Slim Fit Bootcut
While I usually prefer a roomier, more relaxed fit for work jeans, on my days and nights off, I appreciate Levi’s slim fit design. The leaner, sleeker cut is more stylish and looks better paired with a polo, collar shirt, or my favorite leather jacket.
The Levi’s 527 Slim Fit Bootcut jeans deliver the fit I want, but with just enough flaring out of the pant leg to accommodate my cowboy boots.
Though they’re a bit tighter around my waist and thighs, they never feel constricting due to the elastane added in with the cotton.
They’re my go-to jeans with a sleek pair of dress cowboy boots for a date night or meeting up with buddies at a local pub.
What I Like
Slim fit but just the right amount of stretch to remain comfortable.
Boot cut leg is roomy enough to accommodate my cowboy boots.
Light-duty fabric never feels constricting or stuffy.
Budget-friendly.
What I Don’t Like
The denim is thinner and tears more easily than I expected. They’re not the toughest jeans on my list, which is why I typically keep them for social functions rather than work.
What Other Reviewers Say
The Levi’s 527 Slim Fit Bootcut jeans have collected nearly 21,000 reviews, 85% of which are positive. Wearers agree across the board that the cut and fit are superb, and the look is undeniably stylish.
The majority of complaints and negative reviews revolve around the thin, easily damaged denim. Many users are disappointed that the jeans don’t hold up well and are prone to fraying or tearing with high-stress use.
The Verdict
For a night out on the town, the Levi’s 527 Slim Fit Bootcut are my jeans of choice. Comfortable, stylish, and light enough I can dance the night away, these Levi’s are everything I want in a pair of slim-fitting, bootcut jeans.
For a night out on the town, the Levi’s 527 Slim Fit Bootcut are my jeans of choice. Comfortable, stylish, and light enough I can dance the night away (on the slim chance that I choose to). These Levi’s are everything I want in a pair of slim-fitting, bootcut jeans.
Best for Mobility: Levi’s 511 Slim Fit Jeans
The Levi’s 511 Slim Fit Jeans are my top pick for fast-paced days.
The denim fabric incorporates 2% elastane into the cotton, which gives it a surprising amount of stretch.
I’ve used these to play soccer with my kids, run through Costco to check out before the store closes, and lay flooring. They’re just that versatile, thanks to the flexible fabric and the slim cut.
The leg is a bit slimmer than I’d like. It takes a bit of wrestling to pull them down over the top of my work boot, and you can still see a bit of the boot’s outline.
However, for dress boots, the slim fit and slim leg make for a really sleek, stylish look you just can’t get with bootcut or relaxed fit jeans.
Best of all, they’re available in Big and Tall sizes, so I can easily find them in an extra-long size to fit my 6’6” frame (and my oversized waist when I weighed 300 pounds).
What I Like
Slim cut looks very stylish with dress boots.
Elastane blended into the fabric makes for a highly versatile and mobile pair of jeans.
Very comfortable fit, sits nicely below my waist.
Available in a wide range of colors, distressed finishes, and Big and Tall sizes.
What I Don’t Like
The leg is too slim for wide-mouthed cowboy boots.
What Other Reviewers Say
With over 44,000 reviews and a 4.5-star rating, there’s no doubt the 511 Slim Fit Jeans are built right.
Users have called these “the Swiss Army Knife of Pants” for their mobility, versatility, and comfort. The slim fit also earns a lot of praise for being stylish without sacrificing flexibility or being overly skinny.
Sadly, like many of Levi’s newer offerings, the 511s use thin fabric that doesn’t quite hold up to work use and may wear out quicker than expected.
The Verdict
The Levi’s 511 Slim Fit Jeans are the ideal summer jeans because of how light and comfortable they are, not to mention how flexible the fabric is thanks to the addition of synthetic fibers. I’ll throw these on over my favorite pair of dress boots for a night out on the town any time.
Cut slim through the leg, the Levi's 511 slim fit jeans are close and comfortable at the thigh and straight to the ankle. I love the low rise and slouchy top. It's no surprise that these are Levi's bestselling slim fit jeans.
How to Wear Cowboy Boots with Jeans: 3 Style Tips
Pick the Right Cut for Your Specific Cowboy Boots
Cowboy boots tend to flare outward at the top (the mouth), so you need a pair of jeans constructed with a leg wide enough to fit over and conceal the boot tops.
As we talked about in our “Best Jeans for Boots” article, the best cut to wear with cowboy boots are either straight-leg or boot-cut jeans.
However, some slim-fit jeans will have a wide enough leg to conceal your cowboy boots—or, at the very least, pair with a sleeker, less flared-out dress cowboy boot style.
Find the Right Fit (and Length)
The fit will vary depending on your body type:
- Men with a leaner build are better off wearing straight-fit and low-rise jeans that add definition to their legs and highlight their sleek musculature.
- Top-heavy guys with broad shoulders and narrow waists should wear straight-fit jeans that keep their legs from looking too thick for their hips and waist.
- Guys carrying a few extra pounds around their gut will look best in high-rise, straight-cut, or relaxed-fit jeans that define their lower body and help to conceal their midsection.
- Men with wide hips and narrow shoulders should opt for loose, straight-fit, or relaxed-fit jeans to balance out their proportions.
Length is also important to consider when wearing cowboy boots.
The boots’ heels (usually between 1 and 2 inches) will add a bit of extra height, which means you may need a slightly longer pair of jeans than you’d typically wear.
For example, when I wear sneakers, I stick with a 32-inch inseam length. But for cowboy boots, I have to size up to a 34-inch inseam length.
Opt for Darker Denim
Medium to dark-colored Levi’s just look better with cowboy boots, period.
Light-colored jeans pair nicely with sneakers, trainers, slip-on shoes, and casual styles.
But it takes a darker color to hold up to leather cowboy boots.
Conclusion
I cannot overstate the value of not only a good pair of jeans, but “the right” pair.
The right jeans will maximize your style when matched with your boots, shirt, and jacket, will be tough enough to stand up to your daily work and busy life, and keep you comfortable all day long, no matter what you’re doing.
After all my testing, I’ve found the Levis Original 501s to be the best overall jeans to pair with boots. They’re durable, reliable, and offer plenty of room for easy movement while riding, ranching, or working.
The Levi’s Loose Fit 569 Jeans are budget-friendly but surprisingly versatile, while the Levi’s 501 Shrink-to-fit Men’s Jeans deliver the best “bang for my buck” as they mold to my frame and develop a delightful “lived-in” feel the more I wear them.
The Levi’s 527 Slim Fit Bootcut strikes a very nice balance between a stylish slim fit and a roomy leg sized to fit over my boots. I’d consider these not only the best bootcut jeans Levi’s has to offer, but my number two pick overall for wearing with boots.
And you can’t beat the mobility and flexibility of Levi’s 511 Slim Fit Jeans for a fast-paced day.
Possibly the most well-known jeans around, the 501s are the quintessential 'original' Levi's. It's a style that's endured since known since 1873, featuring the original straight fit for an All-American look with a button fly and 5 Pocket Styling.
FAQs
Should jeans be tucked into cowboy boots?
The only time men should tuck their jeans into their cowboy boots is when it’s absolutely necessary—for example if you want to keep your jeans from getting muddy or dirty out on your ranch or farm.
Otherwise, jeans were built to be worn over cowboy boots.
Which Levi’s do cowboys wear?
Levi’s 501s became incredibly popular way back in the 1930s, thanks to their inclusion in early Western films. They’re Levi’s oldest pair of jeans (dating back 150 years) and have been the signature look of cowboys for nearly a century.
When did cowboys start wearing Levi’s?
Initially, Levi’s were worn primarily by farmers, gold miners, and lumberjacks.
However, in the late 1890s and early 1900s, cowboys had begun to abandon their usual pants—leather-lined “California foxed pants,” woolen pants, and corduroy pants—in favor of denim jeans, including Levi’s.
