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One of the worries I have when buying cowboy boots is if they’ll stretch and mold to my feet, what if they don’t and stay tight and rigid forever? It would not only feel like I wasted good money, but my feet would hurt all time. So I decided to try some different boots and see what happens.
Cowboy boots are made to stretch and mold to the shape of your feet. Leather is quite pliable, and over one or two weeks, boots should expand and fit your feet comfortably. Tip: Wearing new boots with thick socks helps quicken the stretching process.
It’s essential when buying boots to understand how much you should expect them to stretch. You don’t want to purchase tight boots and assume they will expand and fit your feet, but after weeks of wear, they never do. So, let’s look at how cowboy boots should fit when they are new and also after you wear them for a while.

How much do cowboy boots stretch?
After buying a pair of new cowboy boots, it takes time for them to stretch and fit your feet. If you purchase boots without understanding how they expand, you’ll likely end up with uncomfortable, ill-fitting boots.
How much cowboy boots stretch depends upon the specific brand, but generally, leather cowboy boots stretch about one-fourth of their initial measurements. However, they only stretch if they fit your feet correctly to start with, and some areas of the boots don’t stretch at all.
When you are shopping, it’s critical to know what parts of the boot are made to stretch. There are at least four parts of the cowboy boots you should be familiar with before choosing a size, the toe, heel, instep, and vamp (ball area).
To begin, you must be aware that cowboy boots don’t stretch much in terms of length. So if any of your toes are in contact with the boot’s end, the boot is too short for your foot and not the correct size.
Remember, there should be a comfortable amount of space around your toes. When you’ve broken in your boots, the distance between the longest toe and interior tip of the boot should ideally be three-quarters of an inch.
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The next area of concern is the heel. People are often confused if heel slippage in cowboy boots is normal or not. It’s intentional and even necessary for your heels to slip somewhat in cowboy boots. However, if your boots are new, you may experience excessive slipping.
If your size is right and you still have an abnormal amount of heel slip, it’s likely caused by a stiff outsole, which refuses to bend when you lift your feet and causes the heel to “slip.” As you use your cowboy boots for a few days, they will lose their stiffness, and the outsole will become flexible enough to bend with the heel.
The third section to check is the boots’ instep; it should be secure from the start. The instep is the upper arch of the foot, between the ankle and the ball. A snug instep is crucial to the effective locomotion and bending of your foot.
When buying your cowboy boots, the insteps shouldn’t feel too loose or too tight. And as you break in your boots, the insteps won’t expand as much as they will mold around your feet.
Finally, the ball of the foot should sit at the widest part of the boot, which should give you the appropriate toe gap and allow you to choose the proper width.
The boot’s ball is covered by the vamp and should fit snug but not tight or cause any pressure. You should be free to flex your foot at the ball easily. Check out my thoughts and suggestions for cowboy boots for guys with wide feet.
When your boots have stretched after use, the balls should only be lightly touching the sides. And, if the ball of your foot doesn’t match up with that of the boot, it’s due to mismatched length, and the boot won’t become wearable even after stretching.
How do you know if your cowboy boots are too small?
If your cowboy boots are too small, you might not know it and decide to wait for them to break in. However, by the time you realize they aren’t meant for your feet, they probably won’t be returnable because you’ve stretched them too much.
Try out different brands and sizes of cowboy boots. If a pair is too small, you will experience abnormal heel slippage, toe pressure, and difficulty when putting them on. Also, consider how the boots will stretch and mold to the shape of your feet as you break them in.
The pair of Ariat Amos cowboy boots, in the picture, that I recently bought were a half size larger than my last pair of Ariat boots. So the first and obvious rule of buying cowboy boots is to put them on yourself.
If you choose your boots based on size number alone, you may run through a lot of boots because not all brand sizes have the same dimensions.
If you have trouble putting on most cowboy boots, it might be because you have high insteps. You can either opt for high insteps cowboy boots or zipper cowboy boots. I personally prefer zippers since they are also much quicker to take on and off.
Your toes should never touch the end of the toe box. If you can’t decide whether the length is appropriate, try hitting a wall with the front of your boots (not too forcefully, of course). If your toes meet the end of the boots. they are too small for you.
The widest part of your feet, called the balls, should feel completely snug. I find this to be the most reliable sign that my feet have found the right boots. If the balls of your feet fit right, it usually determines a proper measure of both the boots’ width and length.
Lastly, you might feel pressure on your ankle while the rest of your foot feels fine. If this happens, I’d advise you to review all the other fitting criteria for cowboy boots. If the boots feel otherwise suitable, the pain may go away with wear.
When I first started wearing my new Ariat Amos boots, they felt a little stiff, and the heel slipped some, but it wasn’t long before they molded to my feet, and now they’re the most comfortable footwear I own.
When shopping for good-looking cowboy boots, quality should be an essential factor. Inflexible leather can be heavy on your feet if you wear it long enough. And if you suffer from painful conditions like plantar fasciitis, cowboy boots with smooth and soft insoles can do wonders.
Do you wear socks with cowboy boots?
Wearing socks with cowboy boots might seem like an alien concept if you’re new to horse-riding. Cowboy or not, I feel my feet very out of place if I am wearing boots without any socks on.
Socks are necessary to get the full experience of cowboy boots. They help prevent your boots from getting stinky due to sweat and heat, make your feet sit much more comfortably, and protect you from blisters and some dangerous health conditions.
Most bootmakers design a boot with extra space for wearing socks. So not wearing a sock can actually be a drawback if a good fit is your priority. Wearing socks can also help if you have difficulty putting on cowboy boots.
Another argument for wearing thick socks is that they can help the boots loosen up faster and more efficiently. When you buy new boots, they exert uncomfortable pressure on your feet, and thick socks can absorb much of this pressure.
Good-quality socks prevent sweat from ruining your boots and your feet. The moist environment might lead to undesirable conditions like athlete’s foot. Wearing boots without socks can also cause blisters and raw spots as your bare feet rub against the boots.
Lastly, socks can provide comfort for your feet. And people that wear socks are less likely to have the skin on their feet harden or crack. The additional cushioning keeps them pain-free at all times. Socks also help maintain better blood circulation by keeping your feet warm.
In general, new cowboy boots only stretch to accommodate for the width, heels, insteps, and calves. They don’t change much in terms of length. Comfort should be your most significant consideration when deciding on the size. And always wear socks with your cowboy boots to stay healthy and enjoy long-term wear.
How do you break in cowboy boots?
The best way to break in a pair of leather cowboy boots is to by wearing them, but if this doesn’t work hold them over a pot of boiling water and let the steam rise into the shaft. Next put the boots on and walks around in them. You can learn some more ideas here:
How to Break In Cowboy Boots to Ride and Walk-in Comfort?
I love animals! Especially horses, I’ve been around them most of my life but I am always learning more and enjoy sharing with others. I have bought, sold, and broke racehorse yearlings. I have raised some winning horses and had some that didn’t make it as racehorses, so we trained them in other disciplines.