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Man wearing ostrich cowboy boots

Whether you’re looking to purchase your first pair of cowboy boots or your new boots have just arrived, we thought it’d be helpful to learn the basics of how they should fit. Maybe it’s our obsession with making sure you’re happy with your purchase or because we know learning how a new pair of cowboy boots should fit can be intimidating. Either way, we’re happy to show you the ropes.

Before we get into how cowboy boots should fit, you should know how to put ‘em on. Sounds silly–we know. But trust us, if you try to put your boots on without the proper technique, you might swear ‘em off for good. We want you to love your boots, so let's take a moment and do it right.

How To Put On Cowboy Boots

  1. When you put your boots on, sit down and loop fingers through the pull straps or grab the sides.
  2. As your foot goes through the turn of the boot, stand up to leverage your body weight. You should feel a whoosh of air leave the boot and hear a “thud” or “plop” as your heel drops into place.

Pro Tip: If your boots have an unlined shaft, they may be a little trickier to slip on. No problem, pardner. Just hook your thumbs on the back of the shaft as you stand up. Pull up on the boot until you feel the air leave the boot and your heel drop into place.

See? Nothin’ to it. Now, let’s talk about proper fit.

How Should Cowboy Boots Fit?

Before we begin, you should know that Tecovas handcrafted western boots are built to deliver a comfortable fit right out of the box and will stretch slightly with wear. They also run true to U.S. sizing, which makes ordering the correct size simple.

For men’s boots, we recommend ordering the size you would typically wear in dress shoes. For women’s cowboy boots, order the size you would typically wear in heels. If you are between sizes, we recommend ordering the smaller of the two sizes, as the leather will give and form to your foot with regular wear. For more sizing information, please check out our cowboy boot size chart.

Now, pull on those boots, and we’ll see if you’ve got the right fit, starting at the toe box.

Toe Box

With your boots on, focus on your toes. Are they set back away from the top of the toe box, and can you move them around without feeling cramped? If so, you’ve got the right fit.

Are your toes cramped or touching the top of the toe box? Tecovas boots are designed with a reinforced toe to help maintain the boot’s shape over time. We recommend sizing up if your toes are cramped or touching the top of the toe box.

Image of brown boot on a shoe shine stand


In a properly fitting boot, the ball of your foot will rest at the widest part of your boot. This helps keep your toes and feet comfortable and prevents tightness or cramping. Our boots are designed with soft leather and cushioned insoles to make ‘em as comfortable as possible.

If you feel any discomfort in the ball of your foot not caused by a pre-existing foot condition, you may benefit from a wider style, like a square toe boot like The Doc pictured below, or a boot in a EE width.

Man wearing brown square toe boots at a rodeo


Now let’s focus on your instep (the top of the foot between the ball and ankle). In a new pair of boots, it’s normal for your instep to feel snug but comfortable–like a firm handshake. Like we said, our boots are meant to be comfortable out of the box, so if you struggle to get your boots on, or once they are on they pinch or squeeze, consider going up a half size or opt-in for a wider style.

The Dean

Man wearing jeans and The Dean boots


When you first try on your boots and walk around, pay attention to your heel. You should notice a quarter to a half-inch heel lift as you walk. As you break in the boot, the outsole will mold to your foot and only make the fit more comfortable over time. If you have no heel lift and your heels are rubbing against the back of the boot, size up. Conversely, if you are experiencing excessive heel slippage and your heel is lifting out of the heel cup, we recommend sizing down.

More Tips To Find Your Most Comfortable Fit

We understand that no two pairs of feet are the same, so why would your boots be? To help ensure you end up with the most comfortable pair of cowboy boots you’ve ever owned, here are a few more recommendations you may find helpful.

Consider Foot Width

One important aspect often overlooked when ordering boots is foot width. Before ordering a pair of boots, consider whether you are more comfortable in boots or shoes with a regular fit or wide fit. If you have wider feet and want extra space, a EE fit may be the right option for you. Currently, all of our women’s boots are available in a B (average) width.

Choose the Right Socks

Socks play a significant role in how well your boots fit your foot. We recommend pairing your cowboy boots with a pair of breathable, moisture-wicking socks that aren’t too tight or thick. Our men’s socks and women’s socks check all of these boxes.

Three pairs of boot socks in varying colors

If You Have a High Instep

High instep? No problem, pardner. Even though most of our boots aren’t explicitly designed for higher insteps, plenty of folks with high insteps find success by sizing up one full size (for men) or half-size (for women).

Alternatively, men’s zip boots like The Dean, The Roy, or The Zane make it easier for folks with higher insteps to comfortably put on, wear, and take off their boots. Women’s zip boots like The Daisy do the same.

The Dean

Man zipping up The Dean boot

If You Need Extra Arch Support

Thanks to our age-old construction methods of shank and lemonwood pegging in the arch area of the foot, Tecovas are universally comfortable for most feet. If you have high arches and would like extra room for your foot to breathe or to place a supportive insert, we recommend sizing up. As is the case for high insteps, zip boots can be a fantastic option for optimal accessibility.

The Daisy

Woman wearing The Daisy bootie

If You Need Orthotic or Special Inserts

Although our insoles are attached to the midsole and not designed to be removed, folks who require special or orthotic inserts have successfully swapped out our inserts with their own. However, we do ask that you wait to remove any original inserts until you are confident you will not be returning or exchanging your boots. For thicker inserts, we recommend sizing up a half size to accommodate the extra room required for a comfortable fit.

Find Your Perfect Fit at Tecovas Today

From answering questions like “How should cowboy boots fit?” to our best advice on Square Toe vs. Round Toe Boots and beyond, Tecovas makes it simple to saddle up in comfort, style, and confidence, knowing the boots you choose are designed to keep you walkin’ tall for the long haul.

If you get your boots and they’re not the perfect fit, don’t sweat it. Our free and easy returns and exchanges means you can swap or send back your boots if you’re not head over heels in love. Just slap on the return label included in the box, and we’ll take care of the rest.

Browse and shop today to find the perfect boots for every adventure–today, tomorrow, and decades down the road.