Cowboy Boots

If you’re wondering how cowboy boots should fit, you’re at the right place. There are several ways to determine how cowboy boots fit that can help you avoid buying ill-fitting footwear you’ll need to return.

However, the process of trying on western boots isn’t like purchasing other types of footwear. That said, here’s a guide on how to fit cowboy boots, plus a few tips on how to stretch them for a faster break-in.

How Should Cowboy Boots Fit?

Cowboy boots fit differently than other types of footwear. Ideally, they’ll be snug but comfortable to support time spent on feet or in the saddle. Note that cowboy boots tend to run slightly large, so you may end up buying a boot size smaller than your standard size.

How the instep feels is the first thing to consider when it comes to how cowboy boots fit. It should be snug enough to keep the heel in place. However, it shouldn’t be so tight that blood can’t freely circulate, as that’s what causes discomfort.

Moreover, the toes should have enough space to wiggle so they aren’t cramped together. When it comes to the heel, a half-inch or less of heel slippage at the outset shouldn’t concern you, as once you break them in, it will adjust. Sometimes, the initial slip is necessary to make room for the boot to accommodate your foot as it wears in.

In addition, cowboy boots have a unique width system for men's and women's styles. Women’s boots are typically sized from A to C:

  • A: Narrow
  • B: Average/medium
  • C: Wide

Men’s cowboy boots are normally sized in B, D, and EE widths:

  • B: Narrow
  • D: Average/medium
  • EE: Wide

Besides the width, several other elements determine how cowboy boots fit, so keep reading to learn more.

How Do Cowboy Boots Fit on Different Parts of the Legs

When looking at how cowboy boots fit, you need to consider your calf, instep, heel, ball, and toes. Here’s how cowboy boots should fit these parts of the leg.


Since cowboy boots go all the way up to the calf, you need to make sure your new boots feel comfortable around this area. That said, the shaft shouldn’t be too tight around your calves, but your ankles shouldn’t have too much room either. Ideally, your boot will have a one to two-inch space around your calf.


The instep refers to the upper part of your foot between your ankles and toes. The instep is the most critical determining factor when looking at how cowboy boots fit. Getting the right fit around the instep is vital as it ensures your heel stays in place, making walking in your boots comfortable. 

That said, the upper part should touch your instep slightly when you put on your cowboy boot. The boot is too small if the leather feels too tight on your instep. However, if it feels too loose, you’ll need a smaller size.

Note that it’s not uncommon for the instep to fit, but to have issues with the heel. At first, it may feel as if your heel doesn’t fit right, which is known as heel slippage. However, this doesn’t have to be an issue. In fact, the heel slip should be there, but not too large. Otherwise, it would mean the boots are too big and you need a smaller size.

If the boot fits well around the instep, the slip will eventually go away as the leather becomes more pliable with wear. If the fit around the instep isn’t right, the leather can cut off the blood supply to the foot, causing a numb sensation. This is a sign you need to replace your boots with wider ones.


Sitting at the widest section of the boot, the ball of the foot is the area where the boot bends when you take a step. The boot is too short if the ball of your foot sits too far forward and will cause discomfort. When boots fit right, the ball of your foot will sit securely within the widest boot part.


New cowboy boots will slip a bit at the heel at first, which is required for the right fit. Eventually, the leather will adjust to the shape of your foot and the slippage will decrease.


The boot’s toe box surrounds the front part of the foot and the toes. Regarding cowboy boots, pressing toes to see whether you have enough room won’t work - it may even damage the toe box. To avoid destroying your new cowboy boots, just wiggle your toes to check whether the fit is right. They should have enough room to move easily within the boot without discomfort.

How to Check Cowboy Boots for Fit

Here’s how to check cowboy boots for fit.

Put on Your Cowboy Boots

When fitting a new pair of cowboy boots, first you need to put your foot into the boot’s shaft and firmly hold the pull tabs or holes. You will hear a muffled popping sound as your foot enters its sitting place once you pull the boots past the resistance point in the arch. The resistance point will come from the top of your foot in the arch area and your heel inside the shaft.

Walk Around to Confirm Fit and Comfort

Once you have your new pair of cowboy boots, walk around in them to make sure you have the right heel lift. Remember that anything more than ⅛ of an inch will mean the boots are too large and anything less will mean your boots are too small.

What’s more, the socks you wear will also impact the way your boots fit, so it’s a good idea to use the same socks you’ll be wearing in the boots. That said, a thicker sock can mean you’ll need a larger boots size, whereas a thinner sock may result in you needing a smaller size.

Cowboy Boots Will Be Stiff at First

High-quality cowboy boots won’t necessarily come perfectly shaped to your foot. While for some people, the boots will fit perfectly from the start, for others, they’ll be stiff at first. Fortunately, as you wear them, the lather and the footbed will adjust to your foot’s shape and will become more comfortable over time.

Can You Stretch out Cowboy Boots?

Cowboy boots will stretch out with wear because the leather will expand. But, if you want to accelerate the break-in process, here are a few tips on how to do that:

  • Wear 2 socks on each foot and keep the boots on for several hours. This way, you will force the leather to stretch and get additional padding. This will, in turn, prevent the leather from rubbing you.
  • Apply the steam to the boot’s inside for a few minutes to soften it. However, be careful because the steam can affect the dye of the leather. As soon as you feel the inside getting softer, stop steaming.
  • Submerge your cowboy boots in water with your hands in the boots. The insole should get a little wet, but be careful not to let the water enter the boots. Water will soften the leather just enough so you can stretch it more easily.
  • If submerging your new boots in water sounds too aggressive, place a water bag inside your boots and keep them in the freezer for at least 8 hours. As the water freezes, it will expand the leather, making your boots more comfortable.
  • You can also use a boot stretching kit that contains a wedge-shaped device and a spray.

How to Style Cowboy Boots

Now that you know how cowboy boots should fit and how to stretch them if necessary, it’s time to learn how to style them. Whether you use them for work, play, or competition, cowboy boots are a fashion piece that deserves to be styled up. Here are a few tips on how to wear cowboy boots for both women and men.

How to Style Cowgirl Boots

Cowgirl boots are much more than just riding boots. And with their rising in popularity, the boot models and accessories have grown to meet demand. Regardless of your lifestyle or fashion taste, there are numerous options for how to style cowgirl boots.

For example, many women wear cowgirl boots with jeans, whether they work at the office or farm. That said, skinny jeans work well with cowgirl boots. Add a stylish top and you’re good to go. You either tuck the jeans into your boots or wear them over your boots, depending on the width of your jeans and personal preferences.

On the other hand, cowgirl boots go well with dresses and skirts as this is the ultimate blend of practicality and femininity.

How to Style Cowboy Boots

Guys have just as many styling options as ladies. The most popular way to wear cowboy boots is with a pair of jeans as that work well whether you’re working on the ranch or going to a bar. When it comes to the jeans cut that goes great with cowboy boots, you can’t go wrong with a bootcut and straight-leg cut. This will give your boots and legs plenty of space without compromising the right fit.

Although jeans go exceptionally well with cowboy boots, chinos and khakis also do wonders. When it comes to the upper part of the body, collared shirts and t-shirts are always a good idea if you pair the colors well.

Wear Your Cowboy Boots with Pride

Cowboy boots are much more than just a fashion statement. They are made to protect your feet in challenging work conditions but are also used for riding, parties, and casual walks. Since some cowboy boots are made of thick and stiff leather, they may feel uncomfortable at first, but they will eventually break in and provide comfort.

With a tradition of 200 years, cowboy boots are highly durable, comfortable, and stylish. With so many styles to choose from, you can find a pair of cowboy boots for numerous occasions whether for work or play. All you need to do is ensure they fit well, and you’re good to go. Just follow our tips and you’ll be enjoying your new boots in no time.

And if you want to buy a new pair, browse our collection of western boots and find your perfect model.