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Should Cowboy Boots Be Hard to Put on? 4 Fitting Tips

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I saw my young grandson struggle to pull on his cowboy boots and told my daughter that he’d outgrown his boots. She responded that cowboy boots are designed to be hard to put on, and his boots fit him fine. Well, I decided to challenge her on that statement.

Broke-in cowboy boots shouldn’t be hard to put on. But new cowboy boots are stiff and require some effort to get your foot in. However, as your feet spend more time in the boots, the leather softens, and taking them on and off should be smooth and easy.

Many first-time cowboy boot owners choose boots based on how they look. But if your boots don’t fit properly, they’ll always be hard to put on. It’s critical to buy the right cowboy boots for your feet.

Cowboy boots that fit shouldn’t be hard to put on.

Putting on a pair of cowboy boots can sure feel weird to first-timers. And unless you were careful, you might end up returning the latest pair of boots you bought because they’re too hard to put on.

picture of a woman struggling to pull on a cowboy boots,

When shopping for cowboy boots, you should try on a bunch of different sizes and brands. By doing this, you get a feel for how different boots fit and should be able to recognize which style and size are best for your feet best.

When I was at Cavendar’s shopping for boots, I was surprised at the differences in sizes between brands and boots’ styles. Some Ariat boots fit that were size 9 and others at size 10.

So you need to be aware of how the sizes run for the boots you want. Perhaps one of the most unrealistic things to expect to happen when buying cowboy boots is coming across a perfect-fitting pair on your first try.

You have to be patient and choose wisely. And once you’ve bought a pair, you can also try different methods to break in your boots faster. The most important thing is that your boots should only be so tight that your feet are comfortable.

My experience with cowboy boots has taught me that a bad fit can cause pain or leave marks even after you’ve taken the boots off.

Choosing your boots.

Specifically, four aspects should be considered when you are looking for a perfect fit.

  • Instep should fit snugly.

The instep of your foot is the arched area that runs between your toes and ankle. The position of the boot that covers this area is called the instep of the boot.

There should be minimum space between the instep of your foot and that of your cowboy boot. However, the instep of your boot shouldn’t be so tight that it makes you uncomfortable.

picture of a new pair of Ariat cowboy boots,

A firm instep is what gives your foot control of the cowboy boots. In fact, in regular boots, the laces’ primary purpose is to ensure that the insteps are close-fitting. In contrast, boots with low insteps can make it difficult for you to put them on.

  • A little heel slip is normal.

Heel slip is pretty basic, it’s the amount your heel slips inside the boot when you take a step. Slippage of approximately half of an inch is normal and acceptable.

You have to have some heel slip because if your heel doesn’t rise at all, it means that your boots’ toes are too tight. And if your boots are too snug, they are uncomfortable and difficult to take on and off.

When you are trying on new cowboy boots, walk around in the store. You should notice a little heel slip when you walk but not much. However, after you break-in your boots, the slippage decreases because as you wear them, the leather forms to your feet.

Here’s a more in-depth read on how tight your heels should fit.

  • The ball of the foot should be relaxed.

The ball is the widest part of cowboy boots and is the area we consider when measuring the boots’ width.

The ball of your foot shouldn’t be pushing too hard against the sides of your boot. It also shouldn’t go so much forward that your toes get squeezed in the toe box.

A simple rule that a good friend shared with me is that the ball of the foot should align with the ball of the cowboy boot. By aligning the ball of your foot with the boot, it will typically guarantee a good fitting in terms of the boot’s width and length.

Check out our recommended cowboy boots for men with wide feet and big calves here.

  • Leave some space at the toes.
picture of a new pair of Justin cowboy boots,

The space between your toes and the inner tip of your boot affects how easy your foot feels. There should be around 3/4th inch of a gap between the longest toe and the end of the toe box.

Personally, if I can curl up my toes without too much difficulty, I know my boots aren’t too short. If there’s an uncomfortable restriction at the toe area, it might be why your feet feel bad in cowboy boots.

It is also worth noting that the toe area of the boots is not meant to be significantly stretched upon use. So, when shopping, you can’t rely on small boots becoming longer or wider at the tips.

Do cowboy boots loosen up?

Any new cowboy boots require a “break-in” period before they can begin to feel at home on your feet. Sadly, I’ve met quite a few people who reject cowboys because they think the boots don’t fit like regular shoes.

However, the truth is that leather is relatively elastic. Cowboy boots are made stiff on purpose so that as you wear them, they can adequately stretch into the individual shape of your feet.

How long it takes for your cowboy boots to loosen up completely depends upon the respective brand and how much you wear them. Generally, if you wear them for a few hours a day, your boots should become fit in 1 – 2 weeks.

If you want to break in your boots quickly, you can try the following:

  • Place a water bag inside the boots, freeze them overnight, and take out the ice in the morning. Repeat this for a week.
  • Heat the boots using a hairdryer, put them on, and walk around until they have cooled back. Do this 5 – 10 times, at least.
  • Wear thick or multiple socks before putting on the boots. The extra layer helps push more forcefully against the boots and loosens them up faster.

However, as mentioned earlier, cowboy boots are meant to be steadily broken in by your feet. I’ve always advised my daughter to endure the break-in period because she will be satisfied with how well the boots fit afterward, delayed gratification at work.

Do cowboy boots hurt at first?

I’ve always been more aware of my feet in a new pair of cowboy boots. What’s more, the balls of your feet feel uncomfortably pressed, your heels keep slipping when you walk, and the soles of the boots seem too stiff.

It is true that, like regular footwear, new cowboy boots will be mildly intrusive on your feet and may even make them numb for a while.

However, the discomfort should not cause you any significant pain as long as the boots are of the appropriate fitting. For instance, if you have trouble putting the boots on or if the vamp feels too tight, you can take a look at some of these cowboy boots for women with high insteps.

The most important thing is to choose the right boot for your foot.

Most Comfortable Cowboy Boots

If it’s comfort what you are after in your cowboy boots, then I suggest you take a look at the cowboy boots I have listed below:

Ariat Men’s Rambler Wide Square Toe Cowboy Boot

Where to buy: Amazon

Customer reviews: 247 customers gave these boots 4.4 out of 5 stars—Amazon Customer Reviews.

The boots have a unique style, and as with most Ariat boots, they have excellent quality thanks to the Duratred outsole and Advanced Stability Torque technology.

Picture of Ariat Rambler cowboy boots,
Buy on Amazon

The gel-cushioned footbed and heel stabilizer offer a comforting experience and minimize shock. You’ll appreciate this feature if you have to run in them or if you work in an environment that’s hard on your feet.

It took me a while to warm up to square toe boots, but now I like the look, and I’ve always been a fan of mid-calf shafts; I find them cooler and more comfortable than boots with tall shafts.

These Ariat boots are good boots for long days working around the barn, look nice enough to wear to town, and make a decent pair of riding boots.The boots are effectively wear-resistant, lightweight, and flexible to support active lifestyles.

Laredo Women’s Miss Kate Western Boot

Customer reviews: 389 customers gave these 4.5 out of 5 stars. See what they have to say.

These decorative women’s boots have a 12 inches long shaft and 1 ¾ inch high heel. The boots pay special attention to western fashion, using contrasting visuals and a snip toe design.

picture of Laredo women's Miss Kate western boots
Buy on Amazon

More importantly, their pure leather insides and cushioned insoles promise comfort and ease. The boots are also an excellent choice for people with wider feet.

Final Words

Like regular boots, cowboy boots should match up with the size and shape of your feet. They need some time to lose their stiffness, and meanwhile, they might feel awkward on your feet. Once they have broken in, however, putting them on and moving in them becomes natural.

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