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5 Most Comfortable Cowboy Boots for Men: Treat Your Feet

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most comfortable cowboy boots

Comfort matters a whole lot when you’re putting in long hours of work on your feet or on horseback. Whether walking, riding, ranching, or farming, you need a pair of boots built to protect, support, and cushion your feet.

Choose from our list of the most comfortable cowboy boots below to make every hard day’s work a more foot-friendly day.

Most Comfortable Overall
  • Quality construction and stylish good looks
  • Versatile design
  • Very likely most comfortable pair of work-friendly cowboy boots you’ll ever own
Best for Flat Feet
  • Good support and cushioning
  • Heritage leather develops a gorgeous patina
  • Comfort insoles combat knee and back pains caused by flat feet
Best for Wide Feet
  • Roomy toe box and spacious interior
  • Extra-thick shock-absorbing cushioned insole
  • Waterproof and available in steel-toe/composite-toe styles
Best Mix of Style and Comfort
  • An ultra-comfortable pair of dress boots
  • Effortlessly stylish and glossy
  • Handcrafted quality
Best Square Toe
  • “Tough” look and solid construction makes for a great pair of work boots
  • Won’t squeeze or constrict your feet
  • A comfortable pair of everyday cowboy boots

If you spend long hours on your feet, comfort should be the most important factor to consider when boot-shopping.

Oh, sure, you also need to take into account things like durability, a design suitable to the work you’re doing, and stability. But really, at the end of the day, the thing that will make or break your boots is how comfortable they are.

In my quest for the “perfect” footwear, I’ve found the best cowboy boot brands are the ones that focus on comfort along with sleek good looks and sturdy construction.

After testing out every pair I could get my hands on, I’ve assembled a list of the most comfortable cowboy boots that will keep your feet snug and comfy over even the longest days of work on your feet or horseback.

How Did I Come Up With My List?

model wearing Tecovas Cartwright cowboy boots
BootSpy testing the Tecovas Cartwright in Bourbon Calf leather.

Cowboy boots are more than just work footwear. Really, they’re a way of life.

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Ranching and farming is incredibly prevalent where I live, which means nearly everyone has at least one pair of cowboy boots tucked away in their closet.

And yes, I am one of those “nearly everyones”.

Granted, I’ve always been a huge fan of the cowboy style (since my dad showed me The Magnificent Seven at age 11). And I mean the whole outfit: ten-gallon hat, collar shirt, massive belt buckle, jeans, and, of course, boots.

wearing camel city mill lightweight socks with cowboy boots
Putting on the Chisos No.2.

I’ve spent years hunting for the most comfortable cowboy boots, testing every pair I could get my hands on, talking to cowboys and ranchers, and researching thousands of customer reviews.

My research has led me to a list of the five boots below. I organized my list to start with the “best” boots (based on comfort) followed by the other pairs I believe will suit a specific need.

5 Most Comfortable Cowboy Boots You’ll Want to Leave On

Most Comfortable Overall: Tecovas Cartwright

Tecovas Cartwright
The Tecovas Cartwright

Tecovas has long been among my favorite brands of cowboy boots. Excellent value for the money, exceptional quality materials, and a broad range of styles to choose from makes it my usual go-to.

So it came as no surprise when I fell instantly in love with their Cartwright boots the moment I slipped them on my feet. Their short break-in time made them easy to start using pretty much immediately. Even now, after years of daily wear, it’s still the most comfortable pair of cowboy boots I’ve ever owned.

Tecovas Cartwright leather sole while walking

It’s pretty much the classic cowboy boot: 12-inch shaft featuring hand-laid cording, 1½” stacked leather heel with just the right angle to be useful for walking and riding, a round toe that slides easily in and out of stirrups, and a look that pairs nicely with my work pants, jeans, or Sunday best.

Comfort-wise, the footbed is supportive and has just enough cushioning for my preferences. The stacked leather heel keeps my feet at precisely the right angle for a long day’s work and the sturdy sole provides a solid, stable base. In my opinion, for the price, it just can’t be beat.

What I Like

  • Available in a surprisingly wide range of materials, from classic calfskin to bovine leather to goat leather.

  • Hand-crafted quality, using high-grade leather from Leon, the “leather capital of Mexico”.

  • All the versatility of the classic cowboy style.

  • Comfortable on every part of my feet, ankle, and calves.

What I Don’t Like

  • The boots (particularly the calfskin) tend to scratch and scuff easily. Over time, though, it adds “character” to the look so I don’t mind too much.

What Other Reviewers Say

With 11,000+ reviews and a 4.8 out of 5-star rating, it’s pretty clear these boots are beloved by wearers. Users compliment their fit (very true to size), short break-in time, great looks, the quality of the materials used, and, of course their comfort, courtesy of the stacked leather heel and integrated arch support.

A few negative reviews spoke of the decorative stitching on the shaft coming loose, which I’ve found to be a common problem with hand-crafted Mexican boots. Other than that, however, wearers didn’t have anything negative to say.

The Verdict

The Tecovas Cartwright just “does it” for me in terms of comfort, durability, style, and quality. Between the short break-in period, the excellent support, and the true-to-size fit, I’m confident you’ll quickly come to agree with my opinion that it’s the most comfortable pair of cowboy boots round.

The BootSpy Tecovas Cartwright YouTube review.

Best Cowboy Boots for Flat Feet: Chisos No. 2

Chisos no1 closeup on street

I spent a lot of time researching boots for flat feet not for myself, but for my youngest son. Even after years of wearing orthopedic corrective shoes, he still needs footwear specifically crafted to maximize stability without excessive arch support (for his very low arches).

The Chisos No. 2 was the pair he settled on after extensive testing. The 1 5/8” heel is a bit higher than the standard cowboy boot, but that actually worked out better for him. There was enough “give” in the leather used for the stacked heel and insole that the boots provided his flat feet more stability. The “comfort insole” just made the fit better-suited to his specific foot shape.

wearing chisos no 1 cowboy boots with jeans

There’s also no denying these are just a good-looking pair of boots: square-toe for a roomier forefoot fit, Goodyear construction, heritage cowhide leather that will patina beautifully, and an 11-inch shaft that matches with pretty much any pair of pants. Plus, they’ve incorporated an 18-gauge steel shank that makes for much more comfortable riding and more stability while walking.  

What I Like

  • The stacked leather heel, leather insole, and comfort insole all work very well for anyone with flat feet.

  • Gorgeous heritage look, and leather develops a luxurious patina.

  • Versatile design that’s suitable for both work and comfort wear.

  • Great stability, support, and fit.

What I Don’t Like

  • The price tag is the highest of all the boots on our list. However, I believe it’s very much a “you get what you pay for” situation where the premium quality is worth the investment.

What Other Reviewers Say

Nearly 500 reviews and a 4.9-star rating says a lot about these boots. Users love them.

Praise for these bad boys emphasize the quality of the construction and the beauty of the heritage cowhide leather. A number of users with problems similar to my son’s (knee and back issues due to flat feet) found the same comfort, support, and stability he did.

On the negative side, there were some mentions of quality control issues (dings, scratches, fraying threads, etc.). A few users had a very hard time breaking in the boots, though that could be due to the wrong fit (a.k.a. too tight for their feet).

The Verdict

My son loves his Chisos No. 2 because they provide support for his flat feet and are comfortable for long, hard work days. The fact that they’re stylish, good-looking, and built to last are all just “gravy”.

Best for Flat Feet
Chisos No. 2

The Chisos No. 2 provides support for flat feet and are comfortable for long, hard work days. The fact that they’re stylish, good-looking, and built to last are all just “gravy”.

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The BootSpy YouTube review of Chisos boots.

Best for Wide Feet: Ariat WorkHog

Ariat WorkHog
The Ariat WorkHog

I’ll be the first to admit my feet are likely to fall into the “too wide” category. It’s rare I find a pair of EE-width boots that don’t fit, and just as rarely a pair of D-width boots that does.

What instantly intrigued me about the Ariat WorkHog boots was the square toe with the surprisingly wide toe box. I took a risk and gave these a try (in D-width), and was blown away to find they fit my wide feet nicely without having to go for the extra-wide sizing.

ariat workhog work boots chainsaw tree

Of course, there were a lot of other things to love about them, too. The DRYShield waterproof construction makes them ideal for those wet and rainy days, and the Duratread sole is slip-resistant on mud, wet concrete, and even oily surfaces. The U-Turn Entry System makes it really easy for me to slip on the boots even with my high arches. 

And when it comes to comfort, I’ve yet to find boots that can match the support and cushioning provided by the ATS Max technology incorporated into the soles of these work boots. There’s even the option to find a WorkHog model with a steel or composite toe. For big, heavy guys (like me) with wide feet (like mine), this is the boot for you.

What I Like

  • Roomy toe box and square toe great for wide feet and long, thick toes.

  • Waterproof, slip-resistant, and very durable.

  • Pressure-dispersing technology in the sole makes for a very comfortable fit.

  •  Sturdy construction that has lasted me for 5+ years of regular use.

What I Don’t Like

  • The break-in period is a bit longer than average (at least, it was for me).

  • The fit around the midfoot can be a little too tight until it’s fully adapted to my feet.

What Other Reviewers Say

Combing through the reviews of these boots, it’s clear they’re a much-loved choice for cowboys who need a versatile, well-built pair of work boots that can handle just about anything life on a ranch, farm, or homestead can throw at you.

Users praise the true-to-size fit and amazing comfort, and the waterproofing is always a big hit with people who work in regions with lots of rainfall. Some actually use them for hunting boots because of how comfortable they are.

A few negative reviews commented on how the color of the boots wasn’t quite right. The boots that arrived were a bit darker than the images on the website. However, a few users noted that the color wears off quickly and the brown leather beneath tends to show through.

The Verdict

If you’re a guy with wide feet looking for a bit more cushioning from their boots, I recommend the Ariat WorkHog. They’re just built tough, comfortable, versatile, and durable: really, everything you want and need in a good pair of work boots.

Best for Flat Feet
Ariat WorkHog

Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.

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We cut the Ariat WorkHog in half to see what’s really going on.

Best Mix of Style and Comfort: Thursday Maverick

I’m going to be up-front with you and say that the Thursday Maverick emphasizes form over function. These are the stylish dress boots you want to keep in your closet for a date night, weekend outing, or formal event. I don’t recommend them for work, however.

Don’t get me wrong: the boots are incredibly comfortable, thanks to their shock-absorbing insoles, adapting cork-bed midsoles, and the 1½” stacked leather heel. You’ll look your absolute best when strutting around town or kicking your heels up in a line dance. 

The full-grain leather oozes effortless style, but it’s not quite tough enough to withstand the rigors of long hours in the saddle or slogging through muddy farmlands.

What I Like

  • The glove leather interior is beautifully soft and won’t cause friction on your feet.

  • The insoles are both shock-absorbing and smell-reducing (Poron antimicrobial foam).

  • You get handcrafted quality and beautiful looks at a very reasonable price tag.

  •  Classic style and glossy leather makes them great dress boots.

What I Don’t Like

  •  The full-grain leather won’t hold up well to work use.

What Other Reviewers Say

Users who tried the Thursday Maverick had largely good things to say about it. Rave reviews highlight the glossy look, the pliability and suppleness of the leather, the short break-in time (1-2 days, according to some), and, of course, their all-day comfort. Thursday’s rapid service also received plenty of praise, with users calling it “the best customer support”.

Really, the only negative reviews I came across spoke about the tight fit. It’s not quite true-to-size, so you may need to go a half-size up or down depending on your foot shape.

The Verdict

For a boot that’s both ultra-dressy and ultra-comfy, I recommend the Thursday Maverick. It combines the glossy, sleek leather exterior with a soft interior, excellent cushioning and support, and long-lasting durability. The antimicrobial lining is also game-changing for guys who tend to sweat a lot (like me). Stinky feet be gone.

Best Mix of Style and Comfort
Thursday Maverick

For a boot that’s both ultra-dressy and ultra-comfy, I recommend the Thursday Maverick. It combines the glossy, sleek leather exterior with a soft interior, excellent cushioning and support, and long-lasting durability. The antimicrobial lining is also game-changing for guys who tend to sweat a lot (like me). Stinky feet be gone.

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Best Comfortable Square Toe Boots: Capitan Cheyenne

Capitan cheyenne boot on foot
The Capitan Cheyenne

I’m a big fan of square-toed boots. While the more “classic” toe for cowboy boots is usually a round toe, snip toe, or pointed toe, square-toed boots tend to be roomier and better able to accommodate my wide forefeet and thick toes. Which, of course, translates to a more comfortable fit and less squeezing over long hours of wear.

Capitan cheyenne

That’s why I fell in love with the Capitan Cheyenne as soon as I pulled them on. The interior gave my feet plenty of room to move around. They don’t have some of the other “comfort” features the other boots I listed above do (no extra insoles or support), but for a simple, practical pair of cowboy boots, they do the job just fine.

What I Like

  • Distressed, “vintage” finish adds a touch of rugged beauty to the cowhide leather.

  • The boots look tough and will last a long time, even for hard-working cowboys.

  • Very roomy interior makes for a more comfortable fit.

  • Every pair of boots is handcrafted and has a unique, exotic look.

What I Don’t Like

  • The style of the shaft is just a little too colorful and flashy for my tastes.

  • Lacking extra support and cushioning in the insoles.

What Other Reviewers Say

Reviews for this boot are largely positive, with real-life customers highlighting their sturdy construction, one-of-a-kind look, and comfortable fit. The price tag (one of the more affordable on our list) was also a big selling point.

A few reviewers with extra-thick calves had a problem with how tight the boots fit around the ankles and leg, though. Some even found them hard to pull off because of the shaft’s narrow construction.

The Verdict

If you want a bit of extra “razzle dazzle” to make your work boots stand out from the crowd, the flair of the Capitan Cheyenne will be right up your alley. Plus, the square toe and wide toe box will give your feet plenty of room to move around and will prevent pinching, squeezing, and crunching. Really, they’re just an all-around solid pair of work boots.

3 Ways to Make Cowboy Boots More Comfortable

1. Get the Size and Fit Right

Capitan lubbock boot

It’s pretty much impossible to expect a pair of boots to be comfortable if they’re the wrong size and fit. You’re all but guaranteeing discomfort from the get-go.

That’s why it’s imperative that you get them just right—not just their length (size), but also their width (fit).

We’ve got a complete and in-depth guide on how to choose the perfect fit for your cowboy boots, but essentially, you can boil it down to a few key points:

  • Give your heel half an inch of wiggle room to avoid rubbing in the back.
  • Make sure the sides of your feet aren’t pinched or squeezed.
  • Choose a style that allows your feet to swell a little (which happens over long hours) without constricting.

It’s worth trying a few different pairs of boots out and exchanging boots until you get the size and fit just right.

How Should Cowboy Boots Fit Diagram

2. Stretch Them Out

Stretching out your boots (from the inside) will expand the leather to the point that you can easily fit your feet inside comfortably, after which point the leather will once again contract and mold to the shape of your feet. It’s an essential part of the break-in process.

As you’ll read in our how-to article on breaking in boots, it’s strongly recommended to use a boot stretcher. You can adjust just how much the leather is stretched so you can improve their comfort without over-stretching (which can leave the boots saggy). To speed up the process, use a blow dryer to (indirectly, from 4-6 inches away) heat up the leather to increase its flexibility.  

3. Clean and Condition Regularly

Cleaning your boots is necessary for their longevity, but your boots also need to be clean in order for leather conditioner to effectively permeate the material. Conditioner will relax and soften the leather fibers, making it easier for you to slide your feet in so the leather will mold to your feet.

However, be aware that using too much conditioner will over-relax the leather and make it saggy. Use it no more than once every 3-4 months for the best results.

Comfort Is a Luxury You Deserve

The right pair of boots won’t just look good and last a long time; it’ll also provide your feet with comfortable protection, support, and stability. Any cowboy who spends long hours riding, walking, or working will agree that comfortable boots are worth their weight in gold. And uncomfortable boots…well, they can make even simple tasks very unpleasant.

For your maximum comfort, I consider the Tecovas Cartwright to be the most comfortable cowboy boots overall. They’re built well, look handsome, but, most importantly, are designed to hug your feet just right and provide good support and cushioning.

For flat-footed guys, the Chisos No.2 is designed just right for the shape of your feet. Guys with wide feet and a heavier build will love the extra-thick cushioning and solid, waterproof construction of the Ariat WorkHog.

Ariat WorkHog

Ariat gave these an apt name. These waterproof work boots are tough. Combine that with Ariat's ATS comfort system, and suddenly working on your feet for 10-12 hours straight is much easier.

Check Best Price Read Our Review
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On those days you want to dress up and stay comfy for long hours, you can’t beat the Thursday Maverick. And the Capitan Cheyenne’s square toe and roomy toe box is just a great all-around choice for guys who need more space to move around in.  


Are cowboy boots comfortable to stand in all day?

The right pair of cowboy boots absolutely will be. Though cowboy boots don’t typically feature quite as much padding and cushioning as work boots, a pair that fits well and is built correctly will offer the all-day comfort and support you need whether you’re standing, working, or riding.

What boots do ranchers wear?

Cowboy boots, of course. Roper boots tend to be the favorite choice of ranchers, thanks to their design that makes them suitable for both riding and walking. However, the traditional Western boot, Western work boots, and walking boots are all great options to consider for a hard day of ranching.

Is it normal for cowboy boots to hurt at first?

Cowboy boots usually hurt at first because the leather is stiff and the fit is intentionally a bit tighter to accommodate multiple foot sizes and widths. That’s why the break-in process is so important. Breaking in the boots means expanding and relaxing the leather enough that it can mold to the unique shape of your foot. Once broken in, cowboy boots will be incredibly comfortable and should provide a pain-free fit.

Say goodbye to sweaty feet.
Say hello to the last boot socks you'll need.
Discover →

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Our Favorite Boot Sock
Camel City Mill Lightweight Wool Work Sock

Made in the USA from Merino wool, these work socks really are something else in terms of quality. They feature compression through the arch and calf which helps your feet recover after a long day. Plus, because they're Merino wool, they're breathable and help reduce foot sweat.

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