Comfortable Cowboy Boots, Whip, an Cowboy Hat in a Desert.

A classic cowboy boot will never go out of style — a true statement supported by the fact that both men and women are still wearing them long after their cultural significance has vanished. And why should anyone stop wearing them? Cowboy boots are testaments to the comfort, style, and ruggedness of the West.

That is why we’ve put together this list of the most comfortable cowboy boots you can find nowadays so that you can relive the glorious past and walk in the shoes (pun intended) of real American legends.

Our list includes six pairs of the most comfortable cowboy boots for both men and women.

Most comfortable cowboy boots for men:

  1. Ariat 
  2. Dan Post
  3. Durango Rebel 
  4. Justin Boots
  5. Rocky


    Most comfortable cowboy boots for women:

    1. Laredo 
    2. Durango
    3. Double H
    4. Ariat 
    5. Justin Boots

      Before we get into our selection of best cowboy boot brands, we’ll explain why they’re so great in the first place.

      How Is a Cowboy Boot Different from a Regular One?

      Most Comfortable Cowboy Boots

      Traditionally, cowboy boots were designed in such a way to make mounting and dismounting a horse much easier. You’ll notice that they have vamps that narrow around the toes, making these boots far pointier than the regular ones.

      However, besides a few design choices that favor horseback riding, cowboy boots aren’t all that different from regular, casual boots. A traditional cowboy boot does feature more details and intricate stitch design that really captures the eye, unlike plain old comfortable work boots.

      Due to their exceptional and stylish design, you can still find numerous brands of cowboy boots to this day. While few people wear them for their function, i.e., getting around on a horse, many prefer them for their incredible look and feel.

      The Western Dilemma: Are Cowboy Boots Comfortable? 

      Nobody wants to put on a pair of ill-fitting boots. Luckily, you can find comfortable cowboy boots without too much effort. But are cowboy boots comfortable to wear all day? By design, these boots are almost always extremely comfortable, provided you get the right size and fit. Since they were made for people spending enormous amounts of time in the saddle and in the great outdoors, you know that comfort was one of the primary concerns and still is.

      Are Cowboy Boots Worth It?

      Getting a comfortable pair of high-quality cowboy boots is an investment like no other. You’ll have footwear that will last you a long time and feel as comfortable as they did the day you bought them. It doesn’t matter if you have wider feet or even flat feet – a good insole, one of the essential elements of the most comfortable cowboy boots, will keep you cushy and accommodate your foot shape.

      Additionally, the most comfortable cowboy boots feature comfortable moisture-wicking lining and soft leather that anyone who plans on wearing these boots for prolonged periods of time will appreciate.

      Can You Wear Cowboy Boots to Work?

      Western Boots for Women


      When it comes to style, you can't go wrong with a pair of classic leather boots. However, in general, cowboy boots don’t have the protective features of regular work boots. They were designed with style and comfort in mind, hence the comfortable lining and a lack of heavy boot features that would harry the rider and the horse.

      However, that doesn’t mean you can’t find brands that make comfortable cowboy boots that are also suitable for work. Enter the modern version of good ol' cowboys. For example, it’s possible to buy steel-toe cowboy boots or ones with durable construction, such as strong welt construction. 

      They also come in oil and slip-resistant leather sole variants for people who work in different environments, and today, you can even find a wide array of waterproof cowboy boots if necessary. These boots will keep your feet dry and protect you against harm. If you need proper work boots, you should know that it’s possible to find durable cowboy boots that will serve the purpose.

      All of the essential elements of a work boot can be included in a pair of cowboy boots – you just have to know what you’re looking for. 

      Top 5 Most Comfortable Western Boots for Men

      Picking out the most comfortable western boots for men and women wasn’t easy. By design, all cowboy boot brands offer incredible levels of comfort that few other types of boots can match. That’s why you should keep an open mind while going through our list and remember that most other cowboy boot brands are just as good. 

      So, if you're wondering, "How do I find comfortable cowboy boots"? just scroll down.


      Ariat men’s Western boots are simply the pinnacle of quality in terms of the most comfortable cowboy boots you can get. They often feature:

      • Full-grain leather: It’s the highest-quality leather you can find in boots.
      • Moisture-wicking linings: Sweaty feet won’t cause any undue problems.
      • Easy-pull cutouts: Ariat cowboy boots for men are super easy to get on or off.
      • Fast break-in period: They’ll conform to your feet in less than a day.

      Dan Post Milwaukee

      Dan Post cowboy boots are known for elaborate stitching, high-quality leather soles, and the comfort cushion insoles. But there’s more.

      • Scalloped topline: Quite a fashion statement that gives these boots a distinct look, which is exactly what cowboy boots are all about.
      • They’re 100% imported leather.
      • Dual pull tabs on the sides: They’ll make putting on your pair of Dan Post Milwaukee boots a breeze.
      • Some models feature a supportive 13″ tall shaft.

      Durango Rebel

      Who doesn’t love a rebel? Especially when they’re equipped with shock-absorbing EVA midsole and genuine western-style stitching on the sides, like Durango Rebels.

      • Great work boots: Durango Rebel boots feature several high-quality protective elements, such as a fiberglass shank, slip- and oil-resistant outsole, and abrasion-resistant upper.
      • Four pull-on holes: Any difficulties while pulling your pair of cowboy boots on are a thing of the past.
      • Durango suspension system: It provides incredible comfort and support throughout the day, making these boots more than suitable for a variety of situations.
      • Cushioned and ventilated footbed: A contoured, removable, and ventilated footbed keeps your feet happy and breathing.

      Justin Boots

      Justin Boot company is a name that resonates, and a brand offering some of the most comfortable cowboy boots out there — their handcrafted boots are a staple since 1879. Removable orthotic inserts and flexible rubber outsoles are the name of the game with Justin men’s cowboy boots. But also:

      • J-Flex flexible comfort system: The proprietary tech of Justin boots, J-Flex, makes Stampede Men’s cowboy boots extra comfortable.
      • Justin stabilization tech: Another in-house design tech making Justins a pair of boots that provide exceptional support.
      • Grippy rubber soles: Durable rubber soles that will last you for years to come.
      • Square toes: Protect your toes from getting pinched or worse. Justins are available in moc, composite, and steel-toe styles.

      Rocky Work Boots

      The Rockies are a classic pick for any horserider, but they’re so much more than that. Their elegant yet simple design has so much to tell.

      • Affordable boots: Rocky cowboy boots for men are more budget-friendly than most other options available.
      • Ventilated footbed: Their footbed is odor-free and has decent airflow that will prevent bacterial buildup.
      • Dri-Lex eco lining: It helps wick away excess moisture from the boots.
      • Durable outsole: The abrasion-resistant outsole is extremely durable and can withstand long hours spent outside on rugged terrain.

      Top 5 Most Comfortable Western Boots for Women

      Women’s cowboy boots are just as impressive in terms of quality and comfort as their men’s counterparts. They are more likely to be made of exotic leather than men’s boots and look even more stylish. Exotic leather or not, women’s cowboy boots boast high levels of comfort and elegance.

      Laredo Miss Kate

      While we are focusing on the most comfortable cowboy boots for women here, the Laredo Miss Kate Western boot had to hold the first spot just for its unique and beautiful stitch design consisting of floral decals and light blue color. Also:

      • Different toe styles: You can get Laredo Miss Kate boots in different toe styles, including the square toe, snipped toe, or the pointed toe.
      • Laredo Flex outsole: Like Justin, Laredo boots come with some proprietary designs such as the Laredo Flex outsole that’s ultra-durable and flexible.
      • Comfort: Miss Kate isn’t just a sight for sore eyes. These cowboy boots are among the most comfortable choices for women, thanks to a cushioned insole.
      • Pull tabs: Putting these boots on is easy and fast, thanks to the side pull tabs.


      Durango cowboy boots have garnered a reputation for their exceptional features, making them a top choice for ladies. Durango's Western boots for women remind us of gunslingers and dangerous ladies of the old West. Above all, they're some of the most comfortable cowboy boots out there.

      • X-Treme Comfort footbed: Durango boots feature the X-Treme Comfort footbed, designed to provide all-day comfort. It ensures superior cushioning and support, allowing you to stay on your feet without discomfort, whether you’re walking, riding, or dancing.
      • Arch support: Durango boots offer excellent arch support. Whether you have flat feet or high arches, Durango’s thoughtful design ensures that your feet are well-supported throughout the day.
      • Steel shank and cushioned footbed: Durango’s combination of a steel shank and a cushioned footbed creates a win-win situation for comfort.
      • Rubber outsole: Rubber outsoles add better traction and durability to the mix.

      Double H

      Double H women’s cowboy boots are not only stylish but also packed with features that prioritize comfort and functionality. They combine incredible Western style with comfort and are frequently associated with it, making them one of the most popular choices for ladies. These boots feature:

      • Cushioned insoles: The inclusion of removable cushioned insoles ensures that your feet receive ample support and cushioning throughout the day, whether you’re riding horses or going about your daily tasks.
      • 100% leather: Classic premium leather construction of the highest quality.
      • Ultra-Welt™ with Gel Cell™ footbed: A remarkable feature found in some Double H boot Western models. The strategically placed gel cells in the heel and front of the foot provide shock absorption and reduce impact during walking or standing.
      • Various toe styles are available. Namely, square toes and round toes.


      It goes without saying that all Ariat women’s cowboy boots are just as comfortable and stylish as Ariats for men, with even more intricate designs. If you want the best western boots for you, Ariat is the name of the game. Our top pick for women? Ariat Fatbaby. Why?

      • Extra space: Ariat Fatbaby cowboy boots can accommodate all foot sizes. It’s perfect for women with wider feet that need all the space they can get.
      • 4LR cushioning: These boots have extra layers of footbed for maximum softness and comfort.
      • Duratread outsole: The outer sole is tough and fairly resistant to wear and tear.
      • Lightweight shank: It adds to the stability without increasing the weight of the boot.

      Justin Boots

      Remember Justin boots for men? Their women’s cowboy boots have it all, too. Our top pick? Turquoise Damiana – it retains the beautiful design of original Western boots, especially the pointy toe that was very much necessary to easily mount a horse.

      This western boot is an excellent all-around choice for women who’d like to get as much comfort and elegance as they can out of their cowboy boots for an affordable price.

      • Stacked heel: Justin Turquoise Damiana boots have a stacked heel that not every other cowboy boot can boast.
      • Unique color: It’s not every day you see turquoise boots. They’re quite a sight compared to other color combinations, giving them a unique look and feel.
      • 11″ supportive shaft: That’s quite a shaft height for women’s cowboy boots, providing all the support you could ever need.
      • Stylish stitching and design details: The decor on Justin Turquoise Damiana boots is simply gorgeous. Few boots can match Damianas in sheer elegance.

      Cowboy Boots Are Always a Good Choice

      If you want a pair of the most comfortable cowboy boots stylish enough to be worn on a night out or on a hike through the great outdoors, you’ll be happy to know that you have plenty of choice in the matter.

      A modern cowboy boot has a durable outsole that will keep your feet dry and comfy no matter where you are. Cowboy boots are still an amazing choice in this day and age, and they’re arguably a far more stylish option than all the other boots. Considering their versatility and utility, there really is no reason not to get comfy cowboy boots and wear them wherever you please.

      You can easily find your new favorite boots with the Western charm at Overlook Boots. Comfort, style, protection, durability – we've got the best from the West in our collections. Browse away.

      Cowboy bootsWestern boots