The 7 most Comfortable Square Toe Cowboy Boots in 2020

Square toe cowboy boots always have mysterious looks. They adore your body with the masculine and wild beauty.

Square-toe cowboy boots are a new line of cowboy boots and they are one of the greatest creations of boot makers.

Square toe cowboy boots are not only for men, there are now square toe cowboy boots that are very popular with women. These boots are symbols for rebellious girls with strong personalities.

Although there is still much disagreement about the viewpoint between square toe cowboy boots and traditional cowboy boots. It is indisputable that square toe cowboy boots have brought a new breeze to the focal point of this western USA.

Come on, let’s join us to explore The 7 most comfortable square toe cowboy boots!

Summary of square toe cowboy boots


Unlike traditional cowboy boots that have existed since the 18th century, new-generation cowboy boots such as square-toe cowboy boots have only appeared for the last few decades.

Nevertheless, square-toe cowboy boots are a late childbirth, but they have confirmed their quality throughout the time. With such impressive appearance and great comfort, square toe boots are now popular all over the world.


You can easily find square-toe cowboy boots at Amazon, they exist in Riding boots, Work boots, Stockman and possibly Roper boots.

Cowboy boots brands such as Ariat, Durango, Laredo or Dan Post are very famous and popular for these square toe boots.

In addition to Riding boots with high heels, the remaining cowboy boots are characterized by low heels.

The common point of square-tip cowboy boots is that they get flat, wide sole with arch support.

The shaft of square-toe cowboy boots are not much different from traditional cowboy boots. They are very subtle and detailed, a work of art on them.

In general, square toe cowboy boots are preferred than traditional cowboy boots because they are comfortable and suitable for more types of feet (wide, flat feet, or high arches…).

Besides, traditional cowboy boots outweigh square boots because they are much more convenient for riding horses.

Why should you choose square toe cowboy boots

  • They own perfect appearance

Cowboy boots always give men a strong masculine look. You want to “live like a king” and don’t like to be bound by any rules. You love to pack up and hit the road. It is obvious that you need wild and durable cowboy boots. And square toes boots is the best choice .

Besides, square toe boots are also new options for girls.

These boots honor your independent and energetic style. A pair of masculine boots bring a cool style for girls.

  • Because of their incredible safety and comfort

Square toe cowboy boots are usually very durable and strong, which is typically stockman boots and western work boots.

You are working outdoors all day and want cowboy boots suitable for outdoor activities, these boots are great for you.

I would love to wear square toe cowboy boots for outdoor picnics, barbecue parties. These boots are great!

Read more: What Size Cowboy Boots Do I Need ?

The 7 most comfortable square toe cowboy boots for men

1/ Ariat Men’s Sport Outrider

You are following a dynamic style and love the cowboy boots that have artwork on the boots’ shaft. Then Ariat Men’s Sport Outrider is for you.

The shaft has an extremely detailed six-row stitch pattern. Also, deep scalloped toplines create stylish looks. The stylized pull holes bring an interesting highlight for this boot.

What we like:

  • 100% Leather
  • Rubber sole
  • Deep scalloped topline
  • Air-Mesh Lining
  • 4LR Four-layer footbed

What we don’t like:

  • Very few bad feedback

2/ ARIAT Men’s Tombstone

A six-row stitch pattern on upper is still not enough for you? Here, ARIAT Men’s Tombstone with TEN-row stitch pattern will surprise you by its splendid appearance as a painting of Van Gogh.

What we like:

  • 100% Leather
  • Rubber sole
  • Full-grain leather foot and upper
  • Durable

What we don’t like:

  • When wearing the sole of the boots emits noise

3/ Durango Men’s Rebel DB5444

If the above 2 boots do not satisfy you for its wild appearance. Do not worry, Durango Men’s Rebel DB5444 with distressed color is a good choice for you. I’m sure that this boot will satisfy both your eyesight and your touch when you wear it.

What we like:

  • Rubber sole
  • Full-grain leather
  • Soft mesh lining
  • Cushion flex insole

What we don’t like:

  • Leather is slightly hard

4/ Ariat Men’s Hybrid Rancher

Never think that work boots only have excellent performance, but their appearance isn’t good. This Ariat Men’s Hybrid Rancher will change your mind.

With a cool appearance and exquisite six row stitch pattern on the shaft, who said that work boots are rough?

What we like:

  • Six row stitch pattern
  • Full Grain leather foot and upper
  • 100% Leather
  • Durable

What we don’t like:

  • A bit tight at the ankles if you have big legs

5/ Ariat Men’s Challenger

Ariat Men’s Challenger has a shaft design made from the same cracked leather. It gives you a cool look while retaining the flexibility of the foot. This boot softens your foot with the suede material.

What we like:

  • 100% Leather
  • Rubber sole
  • Goodyear leather welt
  • Five-row stitch pattern
  • Leather Lining

What we don’t like:

  • There are no other colors to choose from yet

What we don’t like:

6/ Laredo Men’s Kane

Laredo has always been very popular with the Western Boot product line. You can see that Laredo Men’s Kane owns a Western American style: simple and generous, delicate but powerful.

What we like:

  • Distressed leather
  • Rubber outsole
  • Removable orthotic insole
  • Hand lacing detail

What we don’t like:

  • We find no bad comments about this boot

7/ Dan Post Men’s Franklin

The Dan Post brand is famous for its western boots. If you don’t believe, look at the Franklin boots and you’ll know right away.

It gets an impressive appearance. The distressed color in all over the boot gives you a masculine, elegant and attractive look by its dusty style.

What we like:

  • Rubber sole
  • Gel-Flex insole
  • Distressed Mad Cat Leather
  • Fit good

What we don’t like:

  • The cushion sole is not too comfortable

The 7 most comfortable square toe cowboy boots for women

1/ Ariat Women’s Round Up

Ladies would love the sophisticated patterns on this boot! Put it on and feel the comfort. This cute boot comes great with any items on your wardrobe. No need to think more, go get one for a fancy outlook now!

What we like:

  • 4LR technology for support and cushioning
  • Full-grain leather foot and upper
  • Synthetic air mesh lining
  • Wide calf for tucking your jeans

What we don’t like:

  • It is better a dress boot than work boot due to angled heel

2/ Laredo Women’s Anita

Pretty decent tan boot with Stockman heel! Laredo never let us down with their craftsmanship. This boot is awesome and comfortable for a sexy style. Such an impressive boot, isn’t it?

What we like:

  • EVA cushioned footbed
  • Removable Cushion orthotic
  • Distressed leather
  • Standard cowboy style

What we don’t like:

  • Only one model

3/ Ariat Women’s Round Up 2

As the top leading in serving rodeo athletes, Ariat Women’s Round Up gives you absolute comfort along with eye-catching appearance.

The color of Yukon Brown color reflects the light very well that you will be the focus of all eyes. And yet, the shaft of these boots also has a four-row stitch pattern. This boot is useful and very delicate for you.

What we like:

  • Full-grain leather foot and upper
  • Four-row stitch pattern
  • 4LR technology
  • Air mesh lining
  • There are many diverse designs

What we don’t like:

  • Pay attention when choosing boots size

4/ Justin Boots Women’s Gypsy Collection

We love dark brown leather and the turquoise piping. Just these two things make the highlight and the magnetic attraction of Justin Boots Women’s Gypsy boots.

In addition, Gypsy has meticulously crafted stitching that confirms the class of Justin brand.

What we like:

  • Clever color choices
  • Rubber sole
  • 100% Leather
  • Meticulously crafted stitching
  • Durable

What we don’t like:

  • Need time to break in

5/ Durango Women’s Drd0104

Let’s enjoy the very interesting cowboy boots from Durango brand.

Durango Women’s Drd0104 is a pair of western work boots but it looks quite interesting. The shaft is adorned with two guns crossing each other. This creates a very cute and eye-catching appearance.

In addition, Durango is also famous for cowboy boots that cradle your feet. You will be surprised.

What we like:

  • Rubber sole
  • Full grain leather vamp, shaft
  • Double row welt stitch
  • Fit well
  • Lightweight

What we don’t like:

  • We have not received any bad feedback about this product

6/ Laredo Women’s Lola Purple

If you are looking for a new pair of boots after looking through boring cowboy boots, an extremely rare Tan – Purple boots will give you a new look.

These are the things that Laredo Women’s Lola possesses, the tan – purple color has a strange alluring charm.

What we like:

  • Stockman Heel
  • Distressed leather
  • Removable Cushion orthotic
  • Rubber sole

What we don’t like:

  • No more unique colors like that

7/ Twisted X Women’s WS Toe Ruff Stock

This boot is so cute!!!! Full brown and floral embroidery bring elegant style. To make you love it more, it fits very well and requires no break-in time. And yes, it is very comfortable for your feet.

What we like:

  • Beautiful design
  • Fit like a hug
  • Comfortable
  • Fit wide calves

What we don’t like:

  • It is kind of heavy

[FAQ] Are square toe boots comfortable?

I don’t know if you guys or cowboy boots collectors think the same as us. But FromTheGuestRoom thinks that the purpose of the manufacturers when creating square toe cowboy boots is to serve people who enjoy the comfort of wearing boots.

Pay attention to the structure of square-toe cowboy boots – Stockman, Western Boots, Work boots or even Roper boots – their heels mostly from low to standard height (1″ to 1.5″).

Besides, the sole of square toe cowboy boots is usually wide, flat (and may have additional arch support). For the outsole, it is usually made of leather or rubber.

And those properties are regularly included in our “what we like” section. You know, such structures provide great comfort and flexibility for the wearer.

Is square toe boots in style?

Square toe boots are always in style now and forever.

Square toe cowboy boots are huge counterweights to traditional cowboy boots. Since they appeared until now, they have divided the cowboy boots lovers into two groups: pointed vs square toe.

Of course, to do that, the influence of square-toe cowboy boots absolutely isn’t small at all.

In our opinion, square toe cowboy boots have overcome many weaknesses of traditional cowboy boots. A pair of square-toe cowboy boots and a faded Khaki pants will be a good choice for you. That combination will give a masculine and strong appearance.

Do not hesitate! Let’s buy yourself a pair of square toe boots!

How do you wear cowboy boots with square toes?

What to wear with square-toe cowboy boots for men?

We can’t remember how many times we answered such questions.

Bootcut Jean, Khaki pants, and or Office Trouser are great choices for men.

Besides, you can combine boots with a leather jacket, jean jacket or sports jacket to increase your masculinity.

As for me, I like bootcut jeans with a pair of square toe cowboy boots and a jean jacket.

You can read more What to wear with cowboy boots men here

What to wear with square-toe cowboy boots for women? Can you wear square toe boots with dresses?

Dress, bootcut jeans and skinny jeans would be an interesting choice for you.

While bootcut jeans and skinny jeans are a certain choice, dress is also an interesting choice that you should think about.

Pull any dress out of your closet, wear it with a pair of square nose cowboy boots, you will definitely be surprised. (hope you will be surprised in a positive way)

In fact, with women, you get a lot of choices to match with cowboy boots than men.

Just take all the things in the closet and try with your cowboy boots, then wait for the best results.

You can read more about what to wear with cowboy boots for women here.

Do real cowboys wear square toe boots?

Why not?

Square-toe cowboy boots embody innovation, new-generation cowboy boots but still retain the classic beauty of traditional cowboy boots.

Never mind that square-toe cowboy boots will take away the essence of real cowboys. No, they won’t.

Cowboy boots cannot define you, YOU are the one who decides your style. Let’s wake up the wild, strong and liberal cowboy nature inside you.

Be a real cowboy, don’t let boots take control of defining yourselves.

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