Our readers support us. This post may contain affiliate links. We earn from qualifying purchases. Learn More
Where can you find the most comfortable cowboy boots to work, walk, and ride in? They are becoming more popular every day. We have some suggestions on where to begin your search.
There was a time in the not-so-distant past when the words Cowboy boots and comfortable did not belong in the same sentence. Made for the saddle, these boots weren’t really made for, ahem, well, walking.
However, over the past several years, boot-makers have set out to change that image. Cowboy boots today have become much more easily worn, and sometimes are even about as comfortable as your favorite pair of regular shoes.
10 most comfortable cowboy boots to walk in:
- Ariat Groundbreaker Work Boot (Men)
- Ariat Rambler (Men)
- Dan Post Men’s Milwaukee (Men)
- Justin Original Workboots Stampede (Men)
- Durango Rebel (Men)
- Laredo Miss Kate Western Boot (Women)
- Justin Gypsy (Women)
- Ariat Probaby (Women)
- Durango Lady Rebel (Women)
- Ariat Fat Baby Heritage (Women)
Everyone’s foot is different, of course, but in most cases, the following boots provide the best in comfort and provide durability, and good looks.
Our choices are broken down into women’s and men’s styles, and there is a link to each style included if you’d like to check them out for yourself.
5 Most Comfortable Cowboy Boots For Men
Ariat Groundbreaker Work Boot
The Groundbreaker work boot is 100% full grain leather with a suede upper, rubber sole, and four-layer footbed for cushioning.
Made with comfort, performance, and durability in mind, it has a lightweight, stabilizing shank to give more support. It also boasts a trademark Duratred outsole to prolong wear. Designed to live and work in, this boot is sure to meet the toughest standards and hold up to a long workday.
Fans of Ariat boots are loyal to the brand, claiming that these boots hold up better than any other comparable brand. They are rebounded for their all-day comfort and are built to last no matter what kind of torture they are put through.
Features:
- 4 RL footbed support and cushioning
- Duratred outsole
- Oil and slip-resistant
Ariat Rambler
A slightly different style but still the same great Ariat quality, the Rambler has Advanced Torque Stability technology, a composite forked shank, and Duratred outsole, beautified by decorative stitching, squared toe, and mid-calf shank.
The gel-cushioned footbed adds comfort, along with a heel stabilizer for shock absorption and support. Imported, it is made of 100% distressed leather.
Features:
- ATS technology
- Pre-worn look
- Scoured Duratred outsole
Dan Post Men’s Milwaukee
Made with handcrafted excellence, the Milwaukee is 100% leather, imported, and has a leather sole. Features include dual pull tabs, elaborate stitching, stacked heel, and a supportive shaft with a scalloped topline. It has a Comfort Cushion insole and cushion comfort technology.
Features:
- 100% leather
- 13″ supportive shaft
- Comfort cushion insole
Justin Stampede Cowboy Boots
In both the original workboot and the regular style, the Justin Stampede boasts the J-Flex Flexible Comfort system and Justin’s Stabilization technology. This boot has removable orthotic inserts and a rubber sole. It is made of 100% leather and constructed for a hard day of work.
Whether you choose the work boot or the regular Stampede, these boots have the good looks and durability to take you anywhere your day demands.
Features:
- Available in waterproof and steel toe syles
- J-Flex Flexible Comfort System
- Abrasion, slip, and chip resistant
- Electrical hazard rated
- Removable orthotic insert
- Justin Stabilization technology
Durango Rebel
The Rebel is another very comfortable cowboy boot made of full-grain leather with a square toe. It has a contoured, ventilated, and removable cushioned footbed.
The Cushion Flex insole accompanies a tempered steel shank and a slip and oil resistant dual density and abrasion-resistant rubber outsole. This cowboy boot is made to outlast anything you throw at it with comfort and style.
Features:
- Full-grain leather
- Fiberglass shank
- Soft mesh lining
- Oil and slip-resistant
- Non-marking rubber outsole
- Cushion flex insoles
5 Most Comfortable Cowboy Boots For Women
Us ladies do lots of hard work around the barn caring for our four-legged friends. The last thing we need are blisters on our feet, so treating ourselves to some comfortable cowboy boots for women is the least we can do.
Laredo Miss Kate Western Boot
Crafted from genuine leather, these comfortable cowboy boots for women are high on both style and comfort. The insides are lined with leather and finished off with a comfortable cushioned insole. A 13-inch shaft protects your lower leg in the saddle, and a snip toe design gives the boot added style.
These boots are also slightly wider than traditional cowboy boots, so they’re ideal for people with wide feet. We think these are some of the best looking boots on the market.
Features:
- Available in different toe styles, including square toe and snipped toe.
- Flexible leather outsole.
- Cowboy or roper heel in 1″ or 1 &1/2″ depending on the style
- Cushioned footbed
Justin Gypsy
Ideal for day to day wear, the Justin Gypsy boot is a very comfortable cowboy boot. The Justin Gypsy collection is one of our favorite brands of cowboy boots as they combine great western styling with outstanding comfort.
A thick synthetic sole provides extra cushion for the footbed and protection from the elements. Whether you’re horseback, around town, or doing farm chores, these comfortable boots will you look and feel great.
Features:
- Available in a square or round toe
- 100% leather with beautiful brogue stitching
- Removable orthotic insoles
- J-Flex flexible comfort system
Ariat Probaby
A really great choice for comfort, this cowboy boot is a personal favorite. Honestly, this boot is one of the most comfortable cowboy boots you will ever wear.
Similar to the Ariat Fatbaby, but with a higher shaft and just slightly narrower toe, it checks off all the boxes for comfort and durability.
It is 100% leather with a rubber sole, low heel, and round toe shape. This durable, long-lasting boot is perfect for daily wear, walking, riding, and keeping up with life.
Features:
- Distressed full-grain leather
- -ATS (Advanced Torque Stability) technology with 3x the support of traditional cowboy boots
- Reinforced saddle vamp
- Abrasion-resistant, lightly cushioned ProCrepe compound rubber sole
- Stirrup friendly
Durango Lady Rebel
This is another boot I have owned, and though this boot probably took a little longer to break in, once it was, it was very comfortable. It’s a great boot for riding, also, with a nice, high, mid-calf length shaft, and distressed full-grain leather.
It comes in many colors as well, and here I have included a brown and tan style as well as a pink and brown style for those who like more color in their wardrobe.
There are also other color variations available if you prefer. A low heel and synthetic sole complete the package on this very wearable boot.
Features:
- Available in steel toe and waterproof styles
- Full-grain leather
- Oil and slip-resistant
- Marking resistant rubber outsole
Ariat Fat Baby Heritage Boots
If you want the most comfortable cowboy boots on the market, the Ariat’s Fat Baby Heritage boots are just that. The Fat Baby collection boots are made comfort as the top priority.
The Everly sole delivers amazing cushion and wear-resistance, making these ideal for people with wide or and flat feet. Certainly our choice for the best casual cowboy boots for women.
Features:
- Duratred outsole for maximum wear resistance and flexibility
- Genuine 100% full-grain leather
- Ariat 4RL technology: four-layer footbed for comfort with a lightweight, stabilizing shank
How to Make Cowboy Boots Fit More Comfortably
- To try on boots, be sure you wear socks of the same thickness you will be wearing them with every day. We recommend boot socks, as they are made to stay in place with the boot giving a little on the heel as well as covering the calf to prevent rubbing on the leg. The socks we recommend are these Ariat Women’s socks.
- Expect the boot to feel a little bit snug. The leather will give a little as you break them in, making them form to your foot.
- There should be only a small amount of slipping in the heel. Over time they will loosen, and if they are too large to begin with, it can cause blisters on the heel.
- Leave a little wiggle room for your toes. This is especially important if you are going with a style that has a slim or pointed toe.
- The instep holds your foot in the boot, so be sure this area of the boot fits you well. Again, it will loosen somewhat with wear.
- The ball of your foot should line up with the widest point on the sole of the boot.
- Most boots fit about the same as any other shoes in sizes, but Ariats tend to run just a little bigger. Some say a half size smaller fits them well in an Ariat boot. It’s always best to try them on if you can.
Frequently Asked Questions
Yes, if you choose a well-fitting pair of boot that suit your style, cowboy boots can be just as comfortable as athletic shoes.
A small amount of movement is okay, but a boot should not move up and down too much on your heel when you walk.
Steaming boots until the leather is warm and pliable is the best option if you need to break them in quickly. Once the leather is soft, wear them around until they are completely cooled. Using a hairdryer to warm the leather can help as well. Just be sure to wear them until they are cool. However, if you find a well-fitting boot, breaking them in shouldn’t be necessary.
Most boots, if taken care of, will last several years, even with constant wear. They may need occasional minor repairs, but a good quality cowboy boot should last no less than two years, even with daily wear. Practicality is what makes a great cowboy or cowgirl gift, and comfortable cowboy boots are just that!
To make them last longer and maintain their suppleness, we recommend cleaning them at least twice a year with a quality leather cleaner or saddle soap. After, add a layer of soft leather oil or conditioner.
You Deserve the Best Cowboys to Walk In
So whether you are looking for a comfortable cowboy boot for work or for play, these are some of the favorite cowboy boots out there for both women and men. The options are endless.
If you’re still stuck on which pair to buy, keep searching for the right one. We recommend sticking to the best cowboy boot brands such as Ariat, Durango, and Justin. You can’t go wrong with any of their boots that feel comfortable to wear.
Also, if you’re a vegan, see our vegan cowboy and cowgirl boots guide here.
Dara
Friday 9th of October 2020
Are any of these OK to wear in snow? Are any of these good for winter?
Dara
Monday 7th of September 2020
Which of these would you recommend for my daughter is 11 yrs old? She does riding lessons and grooming in camp where they really need boots in the barn. She just grew into a women's size 7.5 to 8 in adidas if that helps.