Cowboy Boots Square Toe vs Pointed Toe

There are two very distinct styles of cowboy boots that cowboy boot lovers should notice: cowboy boots square toe vs pointed toe.

This is not the first time we have a review on the cowboy boot toe shape. However, due to the big difference between the two types of toe shape, we decided to have another article.

We will compare development history, advantages and disadvantages, and outfits match with square toe or pointy toe cowboy boots.

Let’s start!

Cowboy Boots Square Toe vs Pointed Toe

What is a pointed toe cowboy boot?

Today, pointed toe cowboy boots are more popular with women than men, because they bring the sharp, impressive design and femininity. These boots have delicate seams with elaborate stitching, which exudes the glamor of the curves from the instep to the toe.
Pointed toe


Pointed toe cowboy boots are the oldest traditional cowboy boots that were popular in the 1950s. Since then they have become more popular and widespread among cowboys. Cowboy boots were used extensively in rodeos as well as night outs in the town.

These boots experienced through the turbulent period and development associated with American history. Pointed toe cowboy boots are unlike the other boots because they are symbols of the popular culture of the American West.

Pros & Cons:

If you love western American history and traditions, worship the wild and distressed style of cowboys – this is the cowboy boots you are looking for!

As time passed, the world’s fashion styles have changed a lot. For instance, pointy cowboy boots are used by women more than men.

With more stylized and innovative designs, pointy boots for women are more feminine especially with sexy curves of the toe shape and the ball of the foot.

Nowadays, women have a lot of choices for pointed boots as this type of boots suit any type of feet and they can be worn in any weather.

Manufacturers have designed boots like Ankle Booties, fatbaby… with shorter shafts than traditional cowboy boots. You can put on easily and match them with many outfits. Such a friendly boot!

Men use pointed cowboy boots for their classic look. They are patriotic Americans and love the popular culture of the western United States.

In fact, to serve a fraction of the number of men (very demanding customers), these boots are designed to be eye-catching and beautiful and mix modern and traditional style.

Many people wonder if our pointy cowboy boots are uncomfortable and constrained for the toes.

The answer is yes. It is an old story, though. Cowboy boot manufacturers are smart enough to realize that …

Traditional cowboy boots are now very comfortable, they have enough room for the toes to be as flexible as possible.

One more point of the pointed toe for horseback lovers is that these boots are designed to support cowboys’ feet to easily slip into the stirrup.

However, the weak point is…

Despite overcoming the aforementioned weakness, the traditional pointed cowboy boots are still unlikely to be suitable for people with flat feet. The high heel (along with the fact that flat feet are wider than the normal feet) may be uncomfortable for the wearer.

Cowboy boots pointed toe goes with …

For women:

It is easy to think. There are skinny jeans, skirts, shorts or any kind of clothes you can imagine that you are going to be extravagant and attractive to go with these boots.

Tips: If wearing long pants like skinny jeans, you should tuck jeans into cowboy boots, which would be more beautiful.

For men:

It is more troublesome. Since it is not a good idea to match pointed cowboy boots with shorts, skinny pants… we recommend Bootcut jeans, khaki or golf pants, instead. (For reasons, you can see here: How To Wear Cowboy Boots For Guys )

As for the bootcut jeans, it is a gift that God gave cowboys. It exists to go with cowboy boots!

Bootcut jeans tight up on the leg and then flare to the end, creating enough room to tuck your cowboy boots into the jeans.

(Remember that if women tuck jeans into cowboy boots, they look beautiful. However, it will be a fashion disaster if men do the same thing)

What is a cowboy boot square toe?


An opposite of pointed toe, it’s square toe.

Although these innovative cowboy boots have recently appeared, they have created a huge wave of popularity in the United States and spread to the world with many outstanding and different features.

Pros & Cons:

A huge counterweight with pointed toe, square toe is extremely popular with men.
Square toe

Contrary to the pointy cowboy boots, square toe cowboy boots – masculine and wild-looking designs – are very popular with men.

These boots are undoubtedly the target of true men.

To comfort for all types of feet and serve any purposes, square toe boot is designed to promote flexibility, durability and sturdy.

Boots suitable for those who like to “pack up and hit the road”, especially with flat and wide sole, low heels.

A bit of dust and scratches will not make this type of boots worse, but it will give the person a cool and dusty look.

Square toe often appears in cowboy boots such as Walking, Workhog, Roper or Stockman …

You can easily find square toe cowboy boots in brands such as Ariat, Durango, Roper …

This toe is very popular with men, how about women?

The answer is the love of square toe cowboy boots has never been reduced for women since it was launched.

For stylish girls, wearing masculine cowboy boots is one of her choices.

Obviously, matching women’s clothes with square-toe cowboy boots will be a bit more difficult than wearing pointed-toe cowboy boots.

One more thing we think is the small weakness of square-toe cowboy boots. According to our survey, square toe cowboy boots are… very difficult for traditional western fans to accept.

(Trust us, the survey has caused a lot of controversies).

Read more: The 10 Best Looking Square Toe Boots

Cowboy boots square toe goes with …

For men, just like pointed toe, wearing square toe cowboy boots with bootcut jeans is the best match.

Besides, this square-toed boots is extremely suitable for Khaki pants – a pair of slightly old and dusty square-toe cowboy boots combined with Khaki pants will create a masculine, dusty beauty for adventurous girls.

How about women? Square toe cowboy boots are not only suitable for skinny jeans, but the combination of it and dress will do magic.

Do not forget to promote your imagination when you want to create a new combination of square toe cowboy boots with other types of things. Creativity makes everything unique and interesting in life

You have 2 classic fashion styles in 1 coordinating way Classic cowboy boots and classic khaki pants This is a great way to wear clothes and an infallible choice. Because of its dusty and strong characteristic color, Khaki has very few choices in work clothes. Khaki pants are usually sewn with a slender shape, with details such as zippers, so they are best for relaxed breaks or outdoor activities. This combination is sure to create a charming and wild style for you

The bottom line

We had a survey on this issue: Square toe vs Pointed toe

The results are crazy, the quarrels between those who love traditional things versus new things are beyond our imagination.

Anyway, be yourself when you want to choose cowboy boots as confidence will bring beauty to cowboy boots and people wear them.

You are all lovers of the western cowboy’s swagger style and confidence, show it! Be strong and keep your head up, stay confident with your chosen cowboy boots. Cowboy boots will naturally promote their beauty.

Do not allow any sarcasm or personal opinions of others to affect your selection. Because it is your money, your decision and your style

The 5 Best Square Toe Cowboy Boots

1/ Ariat Men’s Workhog

When it comes to square toe cowboy boots, be sure to think of western work boots.

Ariat Men’s Workhog cowboy boots are one of Ariat’s very famous products. With the comfort and flexibility for all day working, these boots are not for homebody.

What we like:

  • Self-cleaning
  • Shock absorbing EVA midsole
  • Oil and slip resistance
  • 100% Leather
  • Soft toe

What we don’t like:

  • There was feedback that they were not really self-cleaning

2/ ARIAT Men’s Western Boot

Western boots often have the classic feature of square toe and low heel. You can totally experience the great feeling when wearing western boots. They make you comfortable and complete you with their cool, wild and liberal appearance. As for this boot, it has very beautiful patterns on the shaft. Feel free to choose the suitable one for your style!

What we like:

  • Twelve-row stitch pattern (Amazing)
  • Leather lined
  • Full-grain leather foot and upper
  • Fit: True to size
  • No need to break in

What we don’t like:

  • Be careful when wearing under the rain

3/ Tin Haul Paisley Rocks

It seems that many people don’t know this brand. But Tin Haul will surprise you with amazing cowboy boots.

Tin Haul produces creative and breakthrough cowboy boots that cannot be mistaken for other brands.

This brand has beautiful square toe cowboy boots, this is also the specialty of Tin Haul.

What we like:

  • 100% Leather
  • Leather sole
  • Breathable leather lining
  • Double welt construction

4/ Dan Post Women’s Serrano

Square toe cowboy boots are not just for men, there are many beautiful and feminine square toe cowboy boots for women, such as Dan Post Women’s Serrano.

Serrano gets dreamy purple accents on the shaft and the sole, which attracts every look.

What we like:

  • 100% Leather
  • All leather upper
  • Removable cushion insert
  • Double stitched welt

What we don’t like:

  • It takes time to break in

5/ Tin Haul Shoes Men’s John 3: 16

Here is another square toe cowboy boot for men from Tin Haul. It is very impressive with the distressed leather material along with the cross on the cowboy boots vamp.

Tin Haul boots are always high quality and worth the price.

What we like:

  • Flexible sole
  • Breathable leather lining
  • Leather sole
  • Cushioned insole

The 5 Best Pointed Toe Cowboy Boots

1/ Laredo Men’s 68068 Monty

The pointed toe cowboy boots with metal tips are one of the specialties that you can easily see in the Laredo brand.

Laredo Men’s 68068 Monty has an impressive foot color design – snakeskin print – you will be one of the most outstanding people in Rodeo.

What we like:

  • Cushion insole
  • Foot design
  • Rubber sole
  • EVA cushioned footbed
  • Support shank

What we don’t like:

  • Slightly striking colors, you should only wear to go to the party or dancing

2/ Dan Post Men’s Milwaukee

Simple but classics, traditional and not fussy, these are easily noticed in Dan Post Men’s Milwaukee.

There are many ways for you to use these boots: go to the office, go out, picnic, horseback riding… all you can think of.

Dan Post’s western boots are simple but world-class.

What we like:

  • 100% Leather
  • Leather sole
  • Cushioning EVA layer
  • Shank stabilizer
  • Fit: True to size
  • Simple design easy to coordinate

What we don’t like:

  • The leather of boots is a bit hard

3/ ARIAT Women’s Round Up Johanna

ARIAT Women’s Round Up Johanna is extremely impressed with the very large feather pattern on the shaft of cowboy boots.

In addition, the boots have a subtle gold thread design that will enhance the feminine look and momentum for girls.

What we like:

  • Full-grain leather foot and upper
  • Rubber sole
  • Fabric lining
  • Fit: True to size
  • Perfect to wear for wedding

What we don’t like:

  • The pointed toe is a bit narrow

4/ Cambridge Select Women’s

A pair of Ankle boots will give you a new look compared to traditional high-shaft-cowboy-boots.

These pairs of ankle cowboy boots have many outstanding features such as absolutely perfect for girls with big calves, easy to put on or take off…

Versatile for any seasons, why don’t you buy a pair of ankle boots?

What we like:

  • Super cute
  • Easy on/off
  • Lightly padded footbed
  • Great to wear with white dress
  • Suitable for all seasons

What we don’t like:

  • You should pay attention to the size, some feedback that they are a bit narrow

5/ Cambridge Select Women’s 2

Take a close look at these boots, this is a perfect example of a traditional cowboy boot.

Cambridge Select cowboy boots feature a 2.25″ high heel design with pointed toe, metal-covered tip. This is the standard design of a traditional cowboy boot.

We especially love these cowboy boots with heels at a height of 2.25″, enough for you to feel confident like a real cowboy but not to upset your feet because it’s not too high.

Besides, the red color will steal the heart of many boys.

What we like:

  • Very stylish
  • Impressive colors
  • Lightweight
  • Inner zip
  • Easy to mix and match

What we don’t like:

  • No other colors to choose

Some comments on the topic: cowboy boots square toe vs pointed toe

1/“I have a few of most toe styles, 40 (+)

I am glad they have so many toe styles, depending on the skin, the color, the shaft height, and the look you are going for, all toe styles have a place and a use.

Be glad we can and have the choice to be independent of each other’s choices!

It would be awfully boring if we all wore the same boot!

Then we wouldn’t need this page because everyone would already have already seen what everyone else is wearing!

Choose your own style/toe ect, feel free to share!

I’ll look! 👍”  – Dave Grogan ( Oh we love this comment )

2/ “I like all cowboy boots, but, to me, square (or the wide square) toe looks l like regular shoes to me. I don’t/wouldn’t notice them as cowboy boots, I would just think they are regular shoes.” – Marc Kos

3/ “Wide square and medium round are the only ones I wear. People on here will give you tons of s**t for liking wide square toe so be prepared for that. But wear what you like man. Its your money and your feet” – Nick Ryan

4/ ”I look at each boot and decide how it looks to me… It just depends on how the particular boot is presented, be it the colors or the leathers or the heels…” – Thomas Hanan

5/ “I’m pointed toe all the way. I feel like square toe makes my legs look stumpy” – Jessica Strom

6/ “The classic look of a pointed toe, will always be the look that we all want.” – Armando Rodriguez

7/ “Unlike the pointed toe and J toe and am a big fan of snipped . I have never owned a big square toe and like never will . Just not for me .” -John Woodrow

8/ “Wide square only for me.” – Brandon Urzendowski

9/ “I only wear traditional cowboy boots. Have for fifty years” – Tim Garrison

10/ “Snip or pointy first, but i like em all” – Monica Pena

11/ “This is one of the very few occasions when I can use this term. I’m very excited…little nervous. I go both ways.” – Michael Brown

12/ “My toes are splayed out, I can only do square toe without breaking them” – Maulin Agrawal

13/ “I personally prefer a wide square toe because of comfort reasons, BUT, the point of wearing cowboy boots it to find what you like and are comfortable with wearing.” – Spencer Sonnier

14/ “I have a variety of toes ranging from wide square to all the way up to a round toe.” – Jeremy Parroco

15/ “Well if we’re able to be honest I despise square toe. I can’t even tell you why I just cringe everytime I see a square toe. I think it’s the ugliest kind of boot no matter what else it looks like, to me square toe ruins the look of any boot. That said pointed toe is pretty strange too. I love a good rounded point. Never ever square.” – Caleb Buhr

16/ “HATE square toe. I’ll sell them but won’t wear them” – Craig Clower

17/ “I think there is a purpose for all toes. I love wide square with relax or extra relaxed jeans. Great for showing or rodeo settings. Round traditional toes for riding with a nice sharp heel and pointier for dressy occasions and slacks or dress suits. Now all can be interchanged, but looks best in the ways I said. My .02” – Derek Knight

18/ “My work/casual boots are square toes, dress boots are medium round, which is my preference. For work I’m not too worried about what my boots look like.” – John Kirby

19/ “Not into square kind all and I don’t usually go for the long pointy ones either. But to each his own and enjoy yourselves.”

20/ “As long as the toe isn’t a foot past my toes then I’m ok with all.” – Alan Eoff

21/ ”Pointed tend to look better, square tend to be more comfortable. I prefer round or J toe… I have all styles however” – Victor Harrelson

22/ “My personal opinion is the square toe aficionado say wear what you like the rest say wear traditional toes. I always viewed square toe boots as work boots and do to this day.” – Justin L. Williams

23/ ”It’s all about comfort really. I don’t cre for Square toe(just my preference) snip toe and J toe fit me best. I have tried a few round toe medium as well as the more pointy round toe. I do have a narrow square toe that fits well.but over all, they just are not as comfortable as the J and snip toe(for me). My wife loves her square toe.” – Edward S. Sheffield

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