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How Should Cowboy Boots Fit? 3 Signs Your Boots Aren’t Right

William Barton

Boots, Leather, Heritage Fashion, Denim, Workwear

William founded BootSpy in 2020 with a simple mission: test and review popular men’s boots and give a real, honest opinion. Since then, we've welcomed over 5 million readers on our boot reviews and boot care guides. Reach out to him for your own personalized boot recommendation at william@bootspy.com. Or join 50,000+ subscribers on the BootSpy YouTube channel, or send him a message on the BootSpy Instagram. Read full bio.

Last Updated: Mar 15, 2024
14 min read

Howdy, partner. Looking for a fresh pair of western-style boots, but you’re not sure how they should fit? 

You came to the right place.

In this article, we’ll break down exactly how your new cowboy boots should fit, and how getting an excellent fit for this style differs from any other boot. 

How The Righ Fit Should Feel

Instep Demonstration on Cowboy Boots

Which part of the foot (and leg) has the most impact in terms of how the boots feel?

The short answer: the instep is the most important factor (that’s the top of your foot, between your ankle and toes). If it’s snug enough to keep your foot back in the heel, but not so tight that you lose circulation throughout the day, chances are you have the right fit—provided that your toes have room, too. 

Don’t worry about the heel so much. You’ll probably have a half-inch of slip in the heel at first. As the leather softens (the cowboy boots break in), that slip will become less and less until you don’t notice it at all. 

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The good news is that cowboy boots don’t really have too harsh of a break-in period. For many brands, western-style boots fit like a glove from the moment you first put them on. 

But you need to get the fit correct first. 

How Should Cowboy Boots Fit Diagram

And—this will sound obvious—the absolute most important thing you can do is choose the right size. Easy to say, harder to do. 

Do Cowboy Boots Run Small?

While it differs from brand to brand, as a general rule, cowboy boots, on average, run slightly large. Be prepared to size down anywhere from a half to a full size, although your best bet is always to do your research for the particular brand you’re considering.

Normally, when you’re buying a pair of sneakers, how do you test the size? I bet you press your thumb down into your toe to make sure there’s about a half-inch to inch of room up front. If it checks out, you’re done.

But most cowboy boots have stiff leather around the toe, or they have a point. This makes it near-impossible to do the “thumb-test.” 

wearing camel city mill lightweight socks with cowboy boots
Wearing my Chisos No.1 boots

And unlike other types of shoes and boots, there are no laces, so you can’t tighten or loosen anything. 

If you need a primer on how all boots should fit, check out our in-depth guide now

But if you already have a good sense on how to pick out the right size, here are a few special considerations you need to make for cowboy boots specifically. 

Correct Calf Fit is Crucial

A classic cowboy boot comes up the calf. This can offer extra protection from the elements (not to mention mud, or worse for those working a farm), but the height can be a real pain if you naturally have large calves. 

author william barton wearing Capitan cheyenne cowboy boots
Wearing my Capitan Cheyenne boots

Since everyone’s calf-size is a little different, there’s no set recommendation for how your boots should wrap around. It’s much more important to get the fit right in the foot and at the toe. 

You may find a half-inch of room at the calf, or you may find up to two inches. Both are acceptable so long as your ankles aren’t rocking around. 

There are a few fixes for if the calves fit too tight on your cowboy boots. The best I’ve found is to use a calf stretcher:

FootFitter Cast Aluminum Combination Boot Instep and Shaft Stretcher
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If your boot is tight around the ankle and instep (top of the foot), but the calf feels ok, you’ll want to try an instep stretcher.

I’ll share more about how to actually stretch the calf of your boots down below if you want to learn more about this method.

Two of the biggest challenges folks face are: one, the boots don’t fit under jeans, and two, the ankle knocks around inside. 

If the ankle of your boot is loose, the boot size is too large. You need to get the correct fit in your instep. Your instep is basically the top of your foot. That should feel snug, which differs from most other types of boots. But because cowboy boots don’t have laces, the instep is what will keep your foot pushed back into the heel. 

Ariat workhog boot in workshop
Wearing my Ariat WorkHogs

If you’re having trouble fitting your boots under your jeans, try getting a straight-cut, or boot-cut jean. 

But if you’d rather just make the calf smaller, you can do that, too. You’ll need a professional’s help.

Tecovas stockton shaft and jeans
Wearing my Tecovas Stockton in Bison leather

Cobblers and boot-repair shops can alter the calf to your preferred size. But once you make the change, it’s done. So make sure you spend some time describing your issue and letting your shoe-repair know exactly what you want.

It’s All About the Instep

Because cowboy boots don’t have laces and most don’t have side-zippers, it’s crucial you get the fight fit in your instep. 

Don’t know what the instep is? No problem. 

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Your instep is the top of your foot, between your ankle and toes. When you put your cowboy boots on, you should feel the leather upper resting snug on that part of your foot. This differs from how other types of boots should fit, but with cowboy boots, you need this to keep your heel secure. 

wearing chisos no 1 cowboy boots with jeans

You may notice some heel slippage at first, which is actually desirable. Over time, as the leather softens up, the slip will go away. You shouldn’t have more than a half-inch of heel slip—if that’s the case, your boots are too big. 

With the right fit in the instep, you may have trouble with your heel at first. We recommend wearing a bandaid or blister pad across your heels for the first few wears until much of that slip disappears. 

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But you can get the right “size” and find that the instep is much too tight and cuts off circulation to your foot. You’ll know this is the case if you start feeling a pins-and-needles effect after wearing your boots a few hours. 

If that’s the case, you may need a wider boot. So if you bought a standard D-width boot, see if your favorite brand carries the same boot in an E, EE, or even extra wide EEE. 

Your Socks Impact How Your Boots Fit

Camel City Mill Heavyweight Socks wool black
The boot-world popular Camel City Mill Heavyweight Boot Socks

The weight of the socks you wear has an impact on how your cowboy boots will fit.

Obviously, the thinner the sock, the more room you’ll have. If you live in a colder climate or prefer wearing heavyweight socks, consider sizing up to account for the extra space the socks will take up.

Alternatively, if you have sweaty feet or prefer wearing lightweight socks, you may want to stay true to size or size down slightly.

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Using the Pull-tabs Helps

Pull-tabs are found on most traditional cowboy boots. Your boots might have pull holes or “mule ears,” which function the same. 

Tecovas stockton bison shaft details

While pull-tabs help get you started, you shouldn’t have to rely entirely on the pull-tab. If you find that you can’t squeeze your foot into your boot without really yanking on the tabs, your boot is likely too small or not wide enough. 

Too much pressure on the tabs can cause them to rip off (it’s happened to us more than once). Pull holes offer a little more durability on this front, but you still shouldn’t absolutely need them to put your boots on. 

You Should Match the Widest Part of Your Boot to the Widest Part of your Foot

Sounds intuitive, right?

Every brand builds their boots a little differently, so it’s important to find a company that can match up their product with your foot. 

Tecovas Cartwright profile view
Wearing my Tecovas Cartwright

If the widest part of the boot lines up with the ball of your foot, chances are you’ll have the right “flex points.” What are flex points? 

Your foot naturally bends in two places: the toe and the ankle. If your boot has a steel shank or some other piece of hardware in a spot where your foot bends, that will cause a lot of pain and it’s not something that can be broken in. 

Most boot manufacturers have a good sense of how to make their boots comfortable for most people, but it’s always good to keep that in mind when you’re shopping around. 

The Toe Shape Impacts Fit

Your toes should be snug yet comfortable and not cramped together. You should have enough room to wiggle them freely, and the cowboy boots’ toe shape can impact this.

Western boots have many different toe-box shapes. You can find square toes, rounded toes, pointed toes, and some dressier cowboy boots even extend out several inches to a point.

model kneeling on one leg with ariat workhog
Hard at work in my Ariat Workhogs

Depending on your toe-length, some of these styles might not be an option for you. 

For instance, if you have long toes, a stubby square toe might cramp your foot. Likewise, a pointed toe may rub too much along your pinky and big toes. Make a mental note of this when you’re trying your boots on. If it’s even the slightest bit uncomfortable in the store, it will only get worse when you’re out on the town or on the ranch. 

Most cowboy boots are built with some point to their toe, but they’re also built a little longer to relieve some of that friction on the side. If there’s too much toe rub, ask for the next available width. 

Stretching Calf Boots: A Step-By-Step Guide

Method #1: Use a Boot Stretcher

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Step 1: Prepare Your Materials

If you’re investing in an aluminum cast boot stretcher—congratulations, you’re on your way to become a real cobbler. 

This step is more about what you shouldn’t do. 

Don’t wet your boots with water. Don’t shove a potato in them. 

Instead, place the stretcher into the boot.

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Step 2: Apply Pressure

Boot stretchers have a mechanism that makes it easy to ramp up the pressure on the inside of the boot. 

You’ll be stretching the boot in stages to promote an even spread of the natural fibers of the leather. Turn the mechanism so you’re applying gentle pressure to the interior of the boot. 

Once you’ve met some resistance, let the boot rest with the stretcher in for 12-24 hours. 

Step 3: More Pressure?

If you need to stretch your boots more, turn the mechanism to apply more pressure. Let the boot rest for another 12-24 hours.

Continue to repeat this step until the boots feel comfortable. 

If you’ve stretched them too far, they may look a little warped, but your boot leather will bounce back a little if you walk in the heat. The leather fibers will loosen back up and spring into their original shape more. 

Method #2: Apply Leather Stretching Spray

FootFitter Shoe and Boot Stretch Spray
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Step 1: Spray the Interior of the Boot

If you’ve opted to go the cheap and easy route, now is the time to grab your leather stretching spray. 

Saturate the leather with the spray. Don’t over-do it and soak the leather through, but try your best to cover every part of the interior of the boot. This may take between 15-20 sprays, depending on the size of your boot.

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Step 2: Put the Boot On

Put the boots on and wear them around the house. It might feel uncomfortable, but it’s also ~$100 cheaper than getting it done at a cobbler or buying your own shoe stretcher. 

The leather should stretch a fair amount in two or three hours of wear.

If your boots become too uncomfortable during this process, take them off and repeat steps one and two the following day. 

Leather stretching spray does a solid job, but just like the aluminum stretcher, it might take several days to reach your desired width. 

Method #3: Go to a Cobbler

Smiling Cobbler

Professionals know exactly how to stretch leather boots without damaging them. If you’ve read through this guide and you’re not sure you want to risk damaging the leather of your footwear, going to a professional is a safe bet. 

Just tell the shoe repair shop which areas are giving you the most trouble and they’ll return them to you stretched in the right places. 

But if most of your shoes and boots fit too tight around the calf and instep, it worthwhile investing in an aluminum shoe stretcher. It’s an investment up front, but you’ll save a lot of cash by skipping the shoe repair shop after every new pair of kicks comes through your door. 

Boots On, Roper

Now that you know how to pick out your next pair of cowboy boots, there’s nothing to do but to do it. 

Always check the store’s return policy before buying, and if you’d like to spend a day wearing your new boots, try them around the house. That way, they’ll stay scuff-free so you can return them if you find they’re too tight or loose. 

Ultimately, your new cowboy boots may take a few weeks to break in, but once they do, you’ll feel you’re working with an old friend every time you slip them on.


Do you size up for cowboy boots?

No, you shouldn’t need to size any differently for your cowboy boots. Just make sure they fit in the instep (it’s OK if there’s a little heel slip). If you have the right fit there and at the toes, you’re all good. 

How do you know if your cowboy boots are too big?

If you’re experiencing more than a half-inch of heel slip, or if your ankle is knocking around inside your boot, they’re too big. When you’re putting on your cowboy boots, you should feel a little tightness at the top of the boot, which will cause your foot to “pop” in. If you get that right, your cowboy boots likely won’t be too big.

How long do cowboy boots take to break in?

Cowboy boots can take anywhere from a week to a month to break in, depending on how stiff the leather is and how often you wear them. Most cowboy boots are decently comfortable right away, but wear a bandaid or blister pad on your heel and at the sides of your feet for the first few wears until the leather softens. 


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