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Are Cowboy Boots Comfortable?

Even if cowboy boots aren't popular in your region, they may be a great addition to your wardrobe. Here's why you should not deprive yourself of having one.

Different color of cowboy boots

Okay, sure, I wear cowboy boots because I like the way they look. (I’m not a cowboy.) Like NYMag  says, “Step into a pair of cowboy boots and something magic happens: Your weight shifts, you pop one hip out to the side, and suddenly the jeans (or yoga pants) you were wearing become an actual outfit.” 

But life is too short for uncomfortable footwear. I learned this after buying a pair of cute, strappy, high-heeled sandals to wear to a concert. They were a little tight but I thought, “How bad could it be?” Well, I ended up taking them off and literally standing on them for three and a half hours because they hurt so bad.

So if cowboy boots weren’t comfortable, I wouldn’t wear them, period.

Luckily, cowboy boots are comfortable! In fact, they are my go-to footwear because of how they look, but also how good they feel – like pajama bottoms for the feet. There’s a reason people say cowboys sleep in their boots. That always sounded horrible. But now that I’m the proud owner of several pairs, I believe it.

Woman jumping wearing cowboy boots

The reason cowboy boots are so comfortable is that they’re really good for your feet. The heel is designed to reduce pressure on your Achilles tendon, which also takes stress off your ankles. The soles of properly made boots are reinforced with metal from heel to toe, which gives you extra support.

Another reason wearing cowboy boots feels good is that they take on the shape of your feet over time, becoming like a “second skin.” This is true for genuine leather boots, definitely, and for some vegan leather ones too.

Which boots are made for walkin’? Well, that’s a matter of opinion. Some say there is no one type of boot that’s objectively the most comfortable. They say everyone’s feet are different and what feels good to one person may not to someone else.

I’ve actually experienced this. I love high-heeled boots, but I have a friend who says she can’t wear them because they make her feet hurt after an hour. She’s fine in low-heeled boots, though. I’ve heard other people say that low-heeled boots like Stockman, Ropers and Western Work Boots are definitely the most comfortable. But I’ve also heard this is only true if you have flat feet.

A woman wearing black cowboy boots

Toe shape is another controversial area when it comes to boot comfort. Some swear by a wide, square toe. And it’s true that this is the style that fits the most different foot sizes, shapes, and widths comfortably. But I have also found very comfortable boots with both pointed toes and rounded toes.

If you think about it, it really doesn’t make sense that certain toe shapes would be inherently uncomfortable. Why would they make those shapes then?  

While the debate rages on, I will tell you one thing I don’t think anyone, city slicker or cowperson, will argue with. For maximum comfort, the most important thing is getting boots that fit you just right. How do you know if they fit? Well, if possible, try walking in them before you buy them. (And if you’re buying your boots online, check the return policy first.) 

When you first put on new boots, they should feel pretty snug. But when you walk, you should be able to feel them flexing and bending along with your foot. They will get softer and more flexible over time, but if you feel like they’re completely rigid the first time you walk in them, that’s a bad sign.

And they definitely shouldn’t hurt. At all. Be sure there’s some space between the tips of your toes and the end of the boot too. Also, and this is kind of a weird one, your heel should slip up a little inside the boot – ¼ to ½ an inch – when you first try them out. This is because the sole is going to get much more flexible with wearing. As it does, your heel will sink down into it and just stay there. 

This brings me to one last important point about cowboy boot comfort: insoles. In quality boots, you will find two main types of insoles: built-in leather ones and removable foam or gel ones (kind of like the ones you find in a lot of running shoes). Both have advantages. Leather insoles mold to your feet over time, which is comfy, but removable insoles are nice and soft and can be replaced to give your boots that new feeling again.  

Though I’d always admired cowboy boots on other people, I avoided buying my own for years because I was afraid they wouldn’t be comfortable. I’m glad I finally bit the bullet. Now I’m sorry I deprived myself for as long as I did!

Related to: 9 Different Types of Cowboy Boots