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

Cowboy boots 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 vaned. 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 comfortable cowboy boots for both men and women.

For men:

  1. Ariat Heritage Roughstock
  2. Ariat Rambler
  3. Dan Post Milwaukee
  4. Durango Rebel
  5. Justin Stampede
  6. Rocky Long Range


    For women:

    1. Laredo Miss Kate
    2. Teva De La Vina
    3. Justin Gypsy
    4. Ariat Fatbaby Heritage
    5. Roper Riley
    6. Justin Turquoise Damiana

      Before we get into our selection of popular 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 the regular ones. A traditional cowboy boot does feature more details and intricate 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.

      How Comfortable Are Cowboy Boots?

      You can find comfortable cowboy boots without too much effort. 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. 

      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 were the day you bought them. It doesn’t matter if you have wider feet or even flat feet — the comfortable insole that is one of the essential elements of cowboy boots will keep you cushy.

      Additionally, cowboy boots feature comfortable 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


      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. For example, it’s possible to buy steel toe cowboy boots or ones with strong welt construction. They also come in oil and slip-resistant leather sole variants for people who work in different environments and can be made waterproof 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 6 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.

      Ariat Heritage Roughstock

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

      • Full-grain leather. It’s the highest-quality leather you can find in boots.
      • Moisture-wicking. Sweaty feet won’t cause any undue problems.
      • Easy-pull cutouts. Ariat Heritage Roughtsock 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.

      Ariat Rambler

      Another sample from Ariat’s perfect selection of cowboy boots. Ramblers are quite a popular choice for their exceedingly comfortable design and Duratread soles.

      • Ramblers are flexible. They move in perfect sync with your feet. Such coordination will make your feet happy and keep them healthy, avoiding strain or any type of harm.
      • No break-in time. Ramblers will adjust to your feet almost immediately. No need to test wear them ahead of time to ensure they’re a proper fit.
      • Gel-cushioned footbed. Excellent for shock absorption, support, and some additional comfort.
      • 100% distressed leather.

      Dan Post Milwaukee

      Dan Post Milwaukee boots are known for elaborate stitching, a high-quality leather sole, and the Comfort Cushion insole. But there’s more.


      • Scalloped topline. It’s 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.
      • Long 13″ supportive 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 are.

      • Great work boots. Durango Rebel boots feature quite a number of high-quality protective elements such as fiberglass shank, slip and oil resistant, and abrasion-resistant outsole.
      • 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. Keep your feet happy and breathing thanks to a contoured, removable, and ventilated footbed.

      Justin Stampede

      Removable orthotic inserts and a rubber sole are the name of the game with Justin Stampede Men’s cowboy boots. But also:

      • J-Flex Flexible Comfort System. Proprietary tech of Justin boots, J-Flex makes Stampede Men’s cowboy boots extra comfortable.
      • Justin Stabilization tech. Another in-house design tech making Justin Stampedes a pair of boots that provide exceptional support.
      • Rubber soles. Rubber soles are incredibly durable and will last you for years to come.
      • Square toes. Protect your toes from getting pinched or worse. Justine Stampedes are available in waterproof and steel-toe styles.

      Rocky Long Range

      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. Rocky Long Range cowboy boots for men are more budget-friendly than most other options available.
      • Ventilated footbed. The 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 outer sole. The outsole is extremely durable and can withstand long hours spent outside on rugged terrain.

      Top 6 Most Comfortable Western Boots for Women

      Cowboy boots for women 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 comfort here, Laredo Miss Kate Western Boot had to hold the first spot just for its unique 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 side pull tabs.

      Teva De La Vina

      Perhaps the most stylish cowboy boot out there — Teva De La Vina reminds us of gunslingers and dangerous ladies of the old west. Above all, it’s an extremely comfortable pair of boots.

      • Mush® Infused insole. This special insole is the source of Teva De La Vina’s comfort.
      • Ankle strap and a side zipper. For additional stability and to make these boots easy to put on, you have a side zipper and ankle strap that also add to the overall roguish style.
      • 100% leather and waterproof.
      • Rubber outsole. Spider365 rubber outsole adds better traction and durability to the mix.

      Justin Gypsy

      Justin Gypsy cowboy boots combine incredible western style with the comfort so frequently associated with it. These boots have:

      • Synthetic sole. The synthetic sole provides excellent protection against the elements and extra cushion for the footbed.
      • 100% leather. While the sole may be synthetic, the rest of the boot most certainly is not. It’s all real leather of the highest quality.
      • J-Flex Flexible Comfort System. Remember Stampede? Justin Gypsy boots for women feature the same system designed for extra comfort.
      • Various toe styles are available. Namely, square toes and round toes.

      Ariat Fatbaby Heritage

      It goes without saying that Ariat women’s boots are just as comfortable and stylish as Ariats for men. If you want the best western boots for you, Ariat is the name of the game.

      • Extra space. Ariat Fatbaby Heritage can accommodate all feet 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.

      Roper Riley

      Roper Riley 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.

      • Budget-friendly. Roper Rileys are an excellent choice if you’re on a strict budget and can't spend a lot on a pair of cowboy boots.
      • Breathable. They come with breathable leather lining that will help keep your feet cool. Sweaty feet can be a serious issue, especially if you’ll be wearing these boots all day.
      • Side pull tabs. Like quite a few cowboy boots on our list, Roper Rileys also feature side pull tabs. You’ll be able to put them on effortlessly.
      • Padded footbed. It’s what makes this pair comfortable enough to make it onto our selection of the most comfortable cowboy boots.

      Justin Turquoise Damiana

      Justin Turquoise Damiana retains the beautiful design of original western boots, especially the pointy toe that was very much necessary to easily mount a horse.

      • 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, giving them a unique look and feel.
      • 11″ supportive shaft. That’s quite a height for women’s cowboy boots, providing all the support you could ever need.
      • Stylish stitching. 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 cowboys boots comfortable and 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 cowboy boots, and wear them wherever you please.

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