Video ·Jan 19, 2023

How to Get the Perfect Cowboy Boot Fit

"How should my cowboy boots fit?" Use these tips and tricks to get the perfect cowboy boot fit for you!

Steps to fit cowboy boots:

0:15 — Before You Buy
1:00 — Will It Stretch?
2:22 — Leather Matters
3:18 — Toe Shape Nuance
4:07 — The Break In
4:45 — Fixing a Tight Boot
6:00 — Different Sized Feet

How to find your size in Chisos

Our boots are true-to-size, simply order the size that you wear most often in other boots / leather footwear! Or alternatively, a half size down from what you wear in sneakers or athletic shoes; a half size down from what you wear in Nike is a very consistent reference point.

Foot width is also very important! If you have a particularly wide foot or high instep, you may be better suited in an EE width or going a half size up from our typical recommendation. Similarly, if you have a narrow foot or a low-volume instep, you may find that a half size down fits better! In general, if you don’t find yourself having to accommodate for a narrow or wide foot in your other footwear, then you shouldn’t have to worry about it in Chisos either. But if that does sound like you, then size accordingly!

Should a cowboy boot stretch?

When trying on a boot for the first time, it is important to remember that leather is very rigid right out of the box! The leather may feel hard and uncomfortable at first, but it will only get more comfortable the longer you wear them. In terms of fit, we are aiming to check the following three boxes:

Enough space in the toebox, ensuring your toes do not feel cramped or squished together. You should have room to wiggle your toes comfortably inside of the toebox! Slight hotspots at the edge of the toebox are normal, and will dissipate as you break-in the boots.
Handshake snugness across the top of your foot, locking you in place inside of the boot. It should not be painful, but we would rather err on the side of tight rather than loose, since this part of the boot will stretch upwards of a quarter of a size and we want to ensure a snug fit after the boot is fully broken-in.
A little bit of vertical heel slip when you put your weight onto the front of your foot or take a step. Anything less than 0.5 inch or a finger’s width is perfect, this heel slip will diminish over time as the heel counter molds to your heel!

If you are checking all of these boxes, then you are in the correct size! That pair of boots will only get better and better as you put some miles on ‘em.

Some feet are very unique, and won’t be able to check all three of these boxes without a little bit of compromise. In these cases, the most important thing is that the boot fits snugly on both feet, but isn’t so tight that you are in any pain. If the boot fits snugly out of the box, it will stretch and conform to the unique areas of your foot.

How shouldn't a cowboy boot feel right out of the box?

If you find yourself in any of the following situations when trying on boots for the first time, it is a good indicator that you are not in the correct size, and should exchange them for a different size.

Foot is sliding front to back or side to side inside of the boot
If you have so much extra space that you can slide your foot inside of the boot, then that boot is too big and you should go a half size down. Your foot should feel firmly held in place by the vamp and heel counter.
Foot is going numb or losing circulation in your toes
If you are losing circulation or getting a tingling sensation in your toes, then that boot is too small. If the length feels right, but it is just too tight, then go to an EE width. If it feels both too short and too tight, then go up a half size.
Foot is sliding out of the boot when taking a step or putting weight onto the front of your foot
If you are able to step right out of the boot without the heel counter catching your heel, or are getting more than a finger’s width of heel slip, then that boot is too big. We are aiming for no more than a half of an inch of vertical heel slip, to ensure that your heel is in the correct position for the counter to mold around it.
Boot is loose and can be shaken off of your foot
If you can lift your foot off the ground and shake the boot off of your foot or feel it moving around your foot, then that boot is too big and you should go a half size down. We want your foot to be properly locked in place right out of the box, so that you can still have a snug fit after the boot has fully broken-in.

Why do Chisos feel different from other cowboy boots?

We do things a little bit differently in our boots. A typical cowboy boot has its high point in the heel, and low point in the ball of your foot, with a steady decline from the high point to the low point. This shape forces your foot into the front of your boot, and means there is more weight being put on your forefoot. This leads to a large strain being placed on your knees, hips, and lower back, meaning that cowboy boots aren’t the best footwear for your body.

However, in Chisos boots, we use a last with a horizontal heel platform and a curved shank, meaning your heel actually has something to grip onto and distribute your weight across the entirety of your foot. What this does is give you far more arch support and comfort than a typical cowboy boot! It may feel strange at first, like there is a light strain on your arch, but once you adjust to this feeling it will be much better for the longevity of your body as a whole. And once you get used to having this much support, it will be hard to go back to a traditional last!

We also use a half-inch thick triple-density memory foam insole in all of our boots. While a typical cowboy boot just has a hard leather insole, our boots give you the comfort and “squish” of a sneaker, while still providing the durability and aesthetic of a boot. The best of both worlds, so you can be on your feet all day in comfort and style!

When to try on boots for the best fit

Cowboy boot fit can be affected by the time of day and the socks you wear. Your feet swell as the day goes on, so it’s best to try boots on in the afternoon to make sure they can accommodate your feet when they are at their widest. You also might be surprised how much difference a millimeter in sock thickness can make! So wear the socks that you would typically wear with boots when trying them on for the first time.

How will a cowboy boot stretch?

When buying boots, these key parts of the boot will adjust to your foot in slightly different ways:

The vamp, or the part of the boot that covers the top of your foot, has the most leather and will stretch about a quarter of a size.
The toe box is reinforced and won't stretch much, so consider going up a half size if your toes feel cramped. However, slight hotspots are normal on the edge of the toebox and will dissipate as the boot breaks in.
The heel counter is the structural focal point of the boot and will mold to your heel for a tighter fit over time. Up to a half inch of vertical heel slip is normal at first, and will dissipate as you break-in the boots!

Overall the boot should fit snugly across the top, have room for your toes, and have a bit of vertical slip in the back (but you should not be slipping front-to-back). If you are checking these three boxes, then you are in the correct size and those boots should feel like socks in no-time!

Cowboy boot leathers explained

There are lots of different types of animal hides (and some plant-based ones) used to build cowboy boots. Each has its own unique characteristics. Here are guidelines that will cover the typical cowboy boot leathers:

Cowhide is the most common and can stretch up to a quarter size over time. It's the middle of the road in terms of pliability and has a nice firm, yet supple texture.
Reptile hides like Alligator and Lizard don't stretch very much, so the fit needs to be right for you at the start. If you are used to wearing and breaking in cowhide boots, you may need to go a half size up in Reptile hides for the right fit.
Ostrich hides have a lot of give to them over time. Some people even complain that their ostrich boots can get sloppy if they over-stretch. But here at Chisos, we use the highest grade South African ostrich to solve this problem. Our ostrich is thicker and stronger than most, and stretches similar to a cowhide.

Different toe styles for Chisos boots

Chisos offers a variety of toe shapes for you to pick from:

The No. 1 is a medium-shape round toe. Not super narrow, but not big and wide either. A very versatile boot, that will offer similar toespace to a dress shoe.
The No. 2 square toe has a little extra room in the toe box. If you've got a wide forefoot or large bunions, or you just like a bit more room for your toes, then the No. 2 might be a good place to start.
The No. 5 snip toe might look like the end got clipped off, but despite its more narrow shape, the toes don't get squished because we elongate the boot to compensate. It fits very similar to the round toe No. 1.
The No. 6 ropers are a bit different, and have a toebox that is just slightly wider than the No. 1. They are designed so you can run in them and rope down calves, and therefore will fit snugly across a larger portion of your foot than any of our other styles. They will also be tighter at the ankles, which may be tricky for people with higher insteps or low ankle mobility.

The unique shape of your foot may affect which boot you chose. But generally speaking, the fit will be consistent across all toe shapes at Chisos unless you have particularly finicky feet. Regardless, you should be able to find a suitable size in whichever style is calling to you!

Do you have to break-in cowboy boots?

In the past, buying boots meant dealing with pain for months! But no more. At Chisos, we strive for a good fit right out of the box with our proprietary comfort insole system. However, there will still be a short break-in period of a few weeks as the leather components adjust to your feet! Under the comfort insole we have a very thick leather insole that molds to your feet the more you wear them. The full-leather sole also gains flex over time. And finally, a leather heel counter adjusts to give you a custom-fit—all which mean your Chisos get even more comfortable over time.

How to fix a tight cowboy boot

Sometimes a boot fits great front-to-back and in the heel, but is a bit too tight over the instep. This area will stretch as you wear the boot, but if you want to speed up the process, here are some quick tips:

Wear them around the house on carpet to break them in and mold to your feet. Your body heat and movement will help the boot begin to loosen and mold to your feet without scuffing the soles (in case you need to exchange for a larger size).
Put on two pairs of socks, then wear your boots for an hour or so. This may be uncomfortable at first, but once you remove the extra socks, even a few millimeters of stretch could be all you need for the right fit.
Stuff a baseball or similar object into the area of the vamp that feels tight and leave it overnight. This will stretch out the instep and save your feet the pressure of pressing back on the leather to stretch it.

Remember, leather can stretch a lot and adjust over time. And for the right fit, the goal is to have them snug, but not so painfully tight that your feet go numb or hurt.

What about cowboy boots for different sized feet?

For those with feet of different sizes, we suggest you buy the size of boots that fits the larger foot. Chisos uses a removable comfort insole system that allows you to make some easy modifications in order to make the other boot fit more snug.

Remove the Chisos comfort insole from the boot of the smaller foot. It will easily slide right out.
Insert a piece of material, such as a very thin shoe insole, into the boot. Then reinsert the Chisos comfort insole on top of the thinner one. Stacking the two has the effect of making the boot slightly tighter.

If you still have questions, feel free to contact us for help! Another great resource is the Chisos Facebook Community. The folks there offer great advice and tips on getting the perfect boot fit. Part of what makes the Chisos community so dang special. Cheers!

Our love for the great state of Texas—and enthusiasm for cowboy boots—motivates just about all that we do. On this blog, we write about community stories, local news and what goes into making the best damn comfortable cowboy boots money can buy. Y'all make it possible for our little boot shop to exist. Don't hesitate to reach out! Call or text 512-866-7222 or howdy@chisos.com