Any links on this page that lead to products on Amazon are affiliate links and I earn a commission if you make a purchase. Thanks in advance – I really appreciate it!
I have been wearing square toe boots for years, and they are by far the most comfortable boots I have ever owned. They provide more room for your toes and don’t pinch your feet like pointed-toe boots can. Plus, they just look damn good.
In this article, I’ve put together a list of ten square toe cowboy boots that are not only stylish but also comfortable. Whether you’re looking for something to wear on a construction site or out on the town, there’s a pair of square toe cowboy boots on this list for you.
And because comfort is important, I’ve only included boots made from high-quality materials and craftsmanship. So you can rest assured that any pair you choose will last and be comfortable enough to wear all day long. Without further ado, let’s get into it.
Also, Check out: 5 of The Very Best Cowboy Work Boots – Square Toe
Most Comfortable Square Toe Cowboy Boots
Tecovas offers a variety of square-toe cowboy boots that are all comfortable, durable, and stylish. The company’s goal is to provide timeless pieces at an affordable price with the quality you expect from high-end custom bootmakers.
Tecovas was founded in 2015 by Paul Hedrick with the goal of revolutionizing the cowboy boot industry. Tecovas boots are made from the highest quality materials and are designed to last a lifetime.
The company offers a wide range of styles, from classic western to modern, and works with some of the best bootmakers in the world to create its products.
My favorite Tecovas cowboy boots are “The Doc.” And if you’re a person that’s on your feet all day, you’ll appreciate these comfortable square-toe cowboy boots.
The best part about Tevocas-Doc is that you can wear them casually or formally. There is adequate room to wiggle your toes or add cushioned insoles or inserts as needed.
The boot’s 1 ½ inch heel allows plenty of scope for jeans stacking. It also features a contrasting stitch pattern, and you get to choose from bison or bovine leather. But the primary reason Tecovas cowboy boots are so popular great is that they are comfortable enough to wear all day.
What we love about it
- Broad square toe design for extra comfort
- Designed in Austin, Texas, and made in Leon, Mexico.
- Signature toe-stitching
- 4 colors and multiple size options
- Excellent customer service from this popular brand.
Named after the enchanting mountains in Far West Texas, Chisos embodies the true spirit of the American cowboy. This is a relatively new cowboy boot company; however, they focus on comfort; in fact, their logo is “DAMN COMFORTABLE COWBOY BOOTS.”
And I can’t disagree. As soon as you put on a pair of Chisos boots, you can feel they are high quality. I corresponded with the founder of Chisos, Will, and immediately knew he was all about providing the best product for his customers.
These handmade boots conform to the feet to offer maximum comfort. Furthermore, features like removable insoles and ready-to-wear ergonomics make Chisos No.2 the most comfortable square top cowboy boot in our books.
The No.2 square toe boot features beautiful juvenile cowhide leather that lasts long and develops a natural patina over time. The quality of Chisos is par excellence, and the styling and stitching are top-notch.
Thousands of owners rated this exquisitely designed square-toe cowboy boot the most comfortable. Many of them have foot issues like irregularly shaped feet or one foot larger than the other. The Chisos No.2 has suited them all. (Check out the YouTube video at the end of this article that compares Chisos craftmanship to other brands.)
What’s to love
- Heritage leather
- Handmade in Texas
- Two colors and multiple size options
- Removable insoles
- Ready-to-wear ergonomics.
Most Comfortable Square Toe Workboot: Ariats
Ariat is the affordable cowboy boot brand known for using innovative technology in all its footwear. The founder of Ariat began her career in the athletic shoe industry.
This experience prompted her to try and bring the comfort of athletic shoes to the boot market. I think she succeeded. For example, Ariat’s ATS (advanced torque stability) technology supports and cushions your feet as you move.
It also promotes good posture and prevents fatigue which is beneficial for people who have to be on their feet all day. Similarly, the Duratread™ also provides oil and slip resistance.
Ariat offers a few durable yet comfortable square toe models, such as Sierra and Groundbreaker, both are exceptional boots. However, I wear Ariat Workhog wide square toe boots with steel toes.
As you can probably tell from the picture, I put these boots through hell. They feature an extra-wide shaft for men with thicker calves, and if you don’t like the bulkiness of steel toe boots, the soft toe version is built to meet ASTM 2892-11 EH standards.
I also have a pair of Ariat Amos boots; these are exceptionally comfortable square toe cowboy that goes well with slacks or jeans. If you want to see what they look like, scroll past the reviews, and there is a picture of me wearing my Amos square toe boots.
Pro Tip: Check out Ariat’s website before buying boots. I’ve found that they have the latest styles and often at the best prices.
What we love about it
- Available in several sizes
- Engineered for all-day support and comfort.
I know my Luccheses pictured above aren’t square toes; however, I am very familiar with the brand and spoke to a few owners of Lucchese square toe boots. There are no finer boots than Lucchese, and we cannot talk about the most comfortable men’s square-toe cowboy boots without mentioning this brand.
Lucchese handmade boots are made using the finest materials. They are also available in various exotic materials like lizards and anteaters. If you want a pair of the most comfortable men’s square-toe cowboy boots that will last long, then look no further than Lucchese.
The Lucchese Giant Alligator riding boot features a square toe and is handmade in Texas using premium gator leather and lemonwood pegs. Its overlaid pull-tabs make it easier to wear and remove. The boots also feature a 12-inch shaft with double-stitch welt construction.
What we love about them
- The Lucchese Giant Alligators’ are the most comfortable square toe boots made from exotic skin you’ll find anywhere.
- Classic cowboy style with western detailing
- Long-lasting boots with multiple comfort features
Throughout the history of footwear, the beloved American brand Tony Lama features among the world’s best footwear brands.
Tony Lama Bonham Buckaroo Square Toe Cowboy Boots are made of genuine leather. Their deep-cut collar with leather pull-on tabs makes them easy to wear. The wide shank and square toe design make it the most comfortable cowboy boot for men with wide or flat feet.
Tony Lama boots are designed to be worn for formal and casual events. In the saddle, they will provide you with protection and comfort.
What we love about it
- Superior craftsmanship
- Time-tested process
- High-quality materials
- Designed for ultimate, long-lasting comfort.
Justin Boots square-toe boots feature the J-Flex Flexible Comfort System in the insoles. J Flex system consists of a cushioned insole and a triple-density insole board. These features enhance comfort and provide a relaxed fit.
Justin makes a few models of comfortable square toe cowboy boots. For workboots, I like their original stampede pull-on square toe boots. And for a general all-purpose boot, I really like the Bent Rail square toe model. You can’t go wrong with either.
Justin Boots are proudly made in the USA and handcrafted by talented artisans in their El Paso factory. The brand has been around since 1879 and has been crowned the Standard of the West ever since.
What we love about it
- J-Flex comfort system
- Made in the USA
- Looks great and true to fit
Dan Post came into being in the 1960s and soon became synonymous with ‘handcrafted cushion comfort.
Dan Post Manning boots are known for using exotic and premium leathers like python, Caiman, and Ostrich. One of my favorites is the Alamosa Ostrich Square Toe dress boots.
Ostrich is a popular skin because it’s soft and pliable, making it one of the most comfortable boot materials available; the downside is they are also relatively easy to tear.
I bought my wife a pair for Christmas; she loved and wore them all the time, even when riding. I bet it was only a couple of months after I gave them to her she walked into the house with a rip down the vamp of her boots.
She was trail riding a limb stuck in the boot and tore them. These are comfortable square toe cowboy boots but not very durable. And the boot’s board square toe design makes them ultra-comfortable for men with wide feet. Rich color with contrasting embroidery enhances the style quotient of these boots.
What we love about it
- Removable orthotic lining- antifungal and antibacterial
- Elegant, stylish
Twisted X square toe ‘Horseman’ marries comfort and style. It is crafted using a full-grain leather upper and air-mesh lining. Full-grain leather ensures breathability and moisture-wicking properties for all-year use.
Twisted X® patented CellSole® technology is integrated into Horseman’s footbed for max comfort. Its double-stitched storm welt offers protection and comfort against the elements.
The rugged boot is designed to last longer, and features pull holes for easy on/off. I’ve noticed more and more rodeo cowboys sporting this brand, which tells me they are rugged and comfortable.
What we love about it
- Full-grain leather construction
- CellStretch® technology in the toes and heel area
- All-day comfort for work or play
Wolverine’s Rancher Square-Toe Wellington cowboy boots are affordable and long-lasting. Their wide square toe combined with a removable OrthoLite® cushioned footbed provides maximum comfort. The boot is also designed for easy on/easy off comfort. Its moisture-wicking inner lining makes these boots perfect for all-year use.
Moreover, its lightweight cement construction and ultra-light EVA midsole reduce fatigue, making these boots perfect for all-day use.
What we love about it
- Comfortable and affordable boots for people on their toes all-day
- Superior grip due to rubber-lug outsole
- It can be worn casually or formally
- Great for men with wide feet
- Classic cowboy style
Durango boots are one of the market’s most affordable and comfortable square toe cowboy boots. All their boots get high ratings. My favorite is the Durango Rebel. It’s made from 100% oiled, dark brown full-grain leather.
You won’t be disappointed in the craftmanship; the footbed is well-cushioned; it has double welt stitching and a tempered steel shank for added stability. One of my favorite features is the American Flag design on the shaft.
I checked out Durango Rebel’s Amazon customer reviews and noted it had a 4.9 out of 5 stars. You can always learn a lot by reading what customers say about products they’ve used.
What we love about it
- Cushion Flex insole
- Rolled shank area
- Dual-density, translucent rubber graphic outsole
- Soft mesh lining
- Lightweight and flexible molded EVA midsole
- Double row sole stitch
- Distressed full-grain leather foot, collar and pull straps with a faux shaft.
Are Square-Toe Boots More Comfortable Than Traditional Cowboy Boots?
Square toe boots are more comfortable than traditional cowboy boots for the following reasons:
Ideal for people with foot deformities
Square-toe boots provide more room for comfortably wiggling the toes and spreading out the feet. This feature makes them more suitable for those having irregular-shaped feet. Even men with one foot longer than the other tend to find better fit and comfort in square-toe boots.
They are especially recommended for people with wide feet who experience discomfort wearing narrow-toed, rounded, or traditional pointed-toe cowboy boots.
Ideal for people with foot pain/swelling
Many people experience pain and swelling when they wear traditional cowboy boots. This can be prevented by using square-toe boots. The wider design of square toe boots also allows you to use them with gel inserts or removable orthotic footbed lining for greater cushioning.
Better for all-day use
With pointed or rounded toes, you will likely experience foot pain when wearing them on the job all day long. Thanks to the square-toe boot’s roomier design, you can prevent foot pain and feel more comfortable throughout the day, whether in the saddle or walking around the barn.
Suitable for casual and formal events
The square-toe boot is here to stay; it is ideal for pairing with jeans and formal trousers and looks great with stacked jeans and even by tucking the jeans into the boot’s shaft.
Do Real Cowboys Wear Square Toe Boots?
Yes, real cowboys wear square toe boots. However, if you visit rodeos, you will see that a lot of cowboys still prefer to wear pointed-toe cowboy boots, which many believe were the original or the traditional cowboy boot shapes. Boots with a pointed toe design make it exceptionally easy for riders to slide their foot in and out of stirrups.
However, modern cowboys often wear mid-width square toe boots. In my family, we have a few that compete in rodeos, and they wear square toe cowboy boots, and you better not say they aren’t real cowboys.
Do You Size Down in Square Toe Boots?
Cowboy boots fit differently than other types of boots. Irrespective of the shape of the boot’s toe, the cowboy boots should fit you snugly. They should not be too tight or too loose.
With square-toe boots, there is usually a lot more room up front. However, this room should not exceed more than 1/8th an inch. If you tend to experience pain or swelling with pointed-toe boots or simply need a spacious toe area because you have flat or wide feet, then choose ½ a size up. Some men may even need to go up a full size.
If you’re buying your boots online, check the reviews to see if the boots run true to size. If they are known to run larger, you may purchase them in your size. If, after trying them on, they feel loose and uncomfortable, you could get them exchanged for half a size or one size down as needed.
Whether or not you need to size down with square-toe boots also depends on the brand of boots in question. In general, it might be better to buy half a size down in square-toe boots if you do not have any foot irregularities.
Key Takeaways – Most Comfortable Men’s Square Toe Cowboy Boots
Many popular brands of cowboy boots make comfortable men’s square-toe boots. Some of the most popular boot brands for square-toe cowboy boots are Lucchese, Justin Boots, and Ariat. Chisos No.2 and Tecovas – The Doc are especially popular for their extra comfy square-toe boots.
Below is a YouTube video showing cowboy boots cut in half to reveal how they’re made.
FAQs – Most Comfortable Men’s Square Toe Cowboy Boots
Why do some cowboy boots have a square toe?
Square-toe boots are better for riding as they offer more room than traditional pointed-toe boots. They may also offer greater stability in the stirrup and are definitely more comfortable when walking around doing barn chores.
Are square-toe boots out of style?
The square toe may be out of style when it comes to other boot styles. However, as far as cowboy boots are concerned, the square toe design will likely never go out of style.
When did square-toe cowboy boots become popular?
Square-toe boots became popular in the 1930s when people opted for functional design in their footwear after the war.
Are square-toe boots flattering?
Yes, square-toe boots are flattering, and they look great with jeans. You can even wear them with formal trousers.