The Most Comfortable Men’s Cowboy Boots For Men

Shopping for new cowboy boots can be a literal pain. Sometimes it takes a while to break in boots properly, and by then it’s too late to make a return. We’ve compiled a list of the most comfortable cowboy boots for men to help make boot shopping a little easier.

That being said, what constitutes a true cowboy boot? With so many advancements in technical apparel and podiatry, boots have changed a great deal over the years. Although cowboy boots are traditionally made of an upper leather and leather sole, we have included some with modern adjustments due to growing popularity. Feel free to scroll by the rubber soles, but the comfort ratings are through the roof!

Shopping for The Most Comfortable Cowboy Boots For Men

Primary Use

Not all boots are meant for riding. The popular cowboy boot “look” has grown in popularity as many steel toe and other work boots have a cowboy boot design. For our purpose, we are looking at general comfort when you’re on your feet (walking or working), as well as stability and flexion in the saddle. Traditionally, cowboy boots will have a longer heel of approximately 1.5”-2”, and a durable toe box to withstand any possible injuries/missteps from livestock.

Upper Material

Although a leather upper is the industry standard, there are multiple types of leather on the market. Most exotic leathers will only be found on the lower, but some boots use exotics for the entire product, including the shaft. Traditional boots utilize cowhide, but exotics include ostrich, snake, elephant, alligator, and even goat leathers. Leathers can be treated for water resistance, but the toughest leather we’ve seen comes from kangaroo hide. Alligator, for example, lacks stretch but offers extreme durability. Most of the following boots will be standard cowhide, but for a price increase, exotic leathers offer suppleness and durability.


Traditionally, cowboy boot outer soles were made of leather, similar to dress shoes. However, new materials are rising in demand. Are you a traditionalist, or do you have an appreciation for the added stability and traction of rubber? We went ahead and included both on our list while keeping a mostly traditional look.


While we chose to keep our prices moderate, superb quality custom cowboy boots can cost thousands. Here we will look at mid-priced boots (some a little over, some under) available without the wait and price tag of a custom design. Like any other shoe, detail work and materials used dictate the price of cowboy boots.

Shopping for The Most Comfortable Cowboy Boots For Men - Price

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Top 9 Picks For The Most Comfortable Men’s Cowboy Boots

1. Tony Lama Men’s Square Toe Jasper Boots

Simplicity and comfort in and out of the saddle:

These boots encompass the classic Tony Lama look with a modern twist for extreme comfort. It has a 13″ shaft with vibrant contrasting stitching, and a roomy square toe box. The heel is 1.75″, making it a great choice if you spend time on your feet.


  • Comfort package insole
  • Classic heritage Tony Lama look
  • Durable double stitching


  • Decreased traction
Most Comfortable Men’s Cowboy Boots - Tony Lamma

2. Boulet Men’s Saddle Rider Boots

A durable modern twist with a classic look:

This boot looks classic inside and out, but uses a subtle 1″ Stockman heel and a rubber outsole designed to look like leather. This is a great option for folks on their feet. It has a 13″ pull-on shaft and double stitched welt, making it extremely durable. It’s made of premium full-grain leather with a leather sole.


  • Mimics traditional riding cowboy boots
  • Mostly leather
  • Durable


  • Heavier compared to other walking boots
  • Lower heel height for riding

3. Twisted X Men’s Buckaroo Boot

Twisted X footwear delivers a trendy and practical boot:

Another home-run from Twisted X! This full-grain leather boot has a higher 16″ shaft that looks sharp in the saddle, reinforced pull tabs, and a double stitched welt. It features an NWS toe and comes in two widths. The molded rubber outsole makes this a popular design for moisture resistance and gives a little more traction in and out of the saddle without compromising a classic look. Twisted X is consistently”stepping up” their boot game!


  • Stylish and popular design
  • Higher shaft
  • Lower heel height for walking comfort


  • Outsole is rubber
  • Doesn’t work with wide calves
Most Comfortable Men's Cowboy Boots For Men - Twisted X

4. Durango Men’s Rebel DB5444 Western Boot

Extreme comfort and a huge color selection:

The Durango Rebel is loved by both cowboys and non-riders alike. With 9 color options, you’re sure to find the perfect match. It has a decent heel of 1.5″ with a prominent spur rest. The high-tech comfort does take away from traditional boot features, such as the mesh lining (great in hot environments) and the flexible insole. This is a great choice for riders that tend to get foot cramps or lower leg aches in the saddle.


  • Rolled shank area
  • Durable
  • Breathable
  • Great for riding or excessive walking


  • Rubber outsole
  • Shorter shaft (12”)

5. Lucchese Classics Men’s Malcolm Giant Alligator Riding Boot

A taste of luxury without the custom price tag:

Lucchese is known to deliver high-end products, and offer unique leather selections. The Malcolm alligator boot is one of their most comfortable designs, featuring an all-leather sole. This boot has a 1.25″ heel, but only a 12″ shaft. The variation in alligator skin makes each pair unique. As far as durability, alligator skin can last several decades with proper care. However, alligator tends to have less stretch than other leathers, so break-in may feel like a different process.


  • Accommodates wide calves
  • Luxury feel and look
  • Durable


  • Expensive
  • Shorter shaft
Most Comfortable Men's Cowboy Boots For Men - Lucchese Bootmaker

6. Ariat Men’s Turnback Western Cowboy Boot

Multi-purpose boot with a moderate price tag:

These can be dressed up or down, used in the saddle, or in any setting. This 100% leather boot boasts a 13.5″ shaft and a nice size heel at 1.75″. Premium full-grain leather is used on the upper and foot area, and the boot uses a hardy Goodyear leather welt. The stabilizing technology makes this a great pick for someone working on their feet that needs a little support, or long hours logged in the saddle.


  • Nice color selection
  • 100% leather
  • Ample sized shaft and heel
  • Torque stability technology for riding use


  • Expensive
  • Narrower square toe box than other Ariat boots

7. Dan Post Men’s Milwaukee 13″ Boot

Comfort and performance delivered at an economical price point:

Typically, most economical leather boots will have some comfort or fit complaints, but Dan Post delivered with the Milwaukee 100% leather boot! It features several color options and a 13″ shaft, leather sole, and nice heel length of 1.5″. Although the boot opening is wider than similar boots, this is not a great option for wider calves or wide feet given the narrow-rounded toe box. The removable orthotic soles give an extra layer of comfort when on your feet. This simple yet classic design is perfect for someone on a budget but unwilling to compromise quality and comfort.


  • Removeable SoftStrike cushioning
  • All leather


  • Fewer fit options
  • Narrower toe box
  • Less detail
Most Comfortable Men's Cowboy Boots For Men - Dan Post Milwaukee

8. Justin Boots Men’s Bent Rail 13″ Boot

Justin adds modern comfort to a timeless classic:

Available in three color options, this is a home-run boot for someone that demands comfort both in and out of the saddle but doesn’t want to break the bank. A 100% leather boot with a plentiful 1.75″ heel, the Bent Rail boot also uses the J-Flex comfort system. It has a durable double-stitched welt and can accommodate larger calves with a 15″ opening. Justin is known for making quality boots backed by a manufacturer guarantee, in price ranges to fit all budgets. These boots cover all the bases at an affordable price, and you’re sure to get years’ worth of wear time!


  • Very comfortable and lightweight
  • Classic look
  • Made in the USA
  • Adequate heel length


  • Decreased traction

9. Ariat Men’s Heritage Roughstock Western Boot

All-day comfort with a western edge:

It’s no surprise Ariat made the list more than once! A far from cry from “traditional”, we had to include the Roughstock boot on our list due to its unbeatable all-day comfort. Although a limited color selection, these boots have ATS technology for stability and wearability. It has a shorter shaft at 12″, but boasts a full-grain leather upper and foot. This model comes in a square toe pull-on design and is great for someone working on their feet for long hours. Despite the non-steel toe box, these have become a popular work boot for those on the job.


  • Extreme comfort
  • Durable


  • Heavy for riding
  • Rubber sole
  • Lacks traditional appeal
Most Comfortable Men's Cowboy Boots For Men - Ariat

Final Thoughts

Although comfort and technology have come a long way, there is still an appreciation for the art and durability of traditional cowboy boots. Even those opting for something less classic, such as the Twisted X Buckaroos, there is a great boot option to meet everyone’s needs. These are our top picks for the total comfort package- whether walking all day or riding fences from sun up to sundown. What’re the most comfortable non-custom boots you’ve ever owned?

Have friends with horses or someone in the market for western wear? Be sure to share this article before they buy their next boots.

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