The Proper Fitting of a Cowboy Boot

Posted by Green Mountain Horse and Tack on 4th May 2022

We’ve all been wearing shoes since we were knee-high and we know instinctively how a proper fitting pair of shoes should feel on our feet. But if you slip on a pair of cowboy boots for the first time, many people sense that something is very wrong - the boots do not feel like shoes. And it’s true; boots do not feel like shoes on your feet. Nearly everything about the feel of a boot on your foot is different from the feel of a shoe. Why is this? How are they supposed to feel? This article will help you understand the why’s and how’s of a properly fitting cowboy boot.

We’ve fitted thousands of boots to feet, so we have a bit of authority on this subject. In fact, we can tell with 99% certainty if a boot fits a customer by the sound it makes when they pull the boot on - seriously! So whether you’re going to your local bootery or just received your boots from Green Mountain, here is what you should expect when trying on cowboy boots for the first time.

Don’t Care About the Toes
To begin with, unless your toes are getting crunched, don’t worry about where they are in the toe box or how close to the end of the boot they are - your toes have nothing to do with the proper fit of the cowboy boot. The fit of the boot is all in the instep. The instep of your foot is the upward slope on the top of your foot as it merges into your ankle. A proper fitting boot should grip your instep with the snugness of a firm handshake.


Put the boot on and stand up straight. The leather on the instep should be firmly draped over and hugging your instep. If it feels like a vice, or you really had to struggle to get past the instep, it’s too small of a size for you. If it’s loosey-goosey and there’s some play in the leather, it’s probably too big of a size for you. If it’s snug and firm, you can confirm it’s a good fit by locating the ball of your big toe inside the boot. It should be located at the widest part of the sole of the boot, and if the instep is snug, that’s exactly where you will find it. When you pull on a proper fitting boot, as your foot gets past the instep you’ll often hear a “pop”. That’s the sound of a great fitting boot.

Pulling the Boot on
It’s important to pull the boot on correctly too, otherwise you could damage the boot’s pull tabs. The pull tabs are the tabs that are sewn into the top of the shaft of the boot. A lot of boots today have gotten away from sewing pulls onto the shaft and have reinforced holes punched into the top of the shaft, which are virtually indestructible, so this doesn’t really apply to pull holes.

The pull tabs are there to help you get the boot on. The problem is that these are just little pieces of leather sewn onto the shaft. When you use the boot pulls, keep your foot on the floor. Many people feel the need to raise their leg and pull the boot on while the boot is suspended out in front of them. You’ll get the boot on this way, but eventually you’ll rip the stitching and pull off the pull tabs. Keep your foot on the floor as you put the boot on so you don’t rip these off.

If you have trouble reaching down to pull those boots on, invest in a pair of boot pulls, which are little tools that extend your reach down to the boot.

Heel Slippage
As people walk around in cowboy boots for the first time, many times they immediately notice that their heel is slipping, rising off of the footbed as they come out of the back step and prepare to raise their foot off of the floor. Some are convinced this means the boot doesn’t fit. Not true. To understand heel slippage, one must understand that the sole of a boot, out of the box, is much thicker and much less flexible than the sole of a shoe. Boots have traditionally been built to be rugged, tough, and long-lasting - this is one of the reasons people like them so much. Shoes, generally speaking, are built to look good and be comfortable.

The primary reason the heel slips in new boots is because the sole is thick and rigid. Think about it. If you strapped a piece of plywood to the bottom of your foot, your foot would flex in your step and the wood would not, and your heel would lift off the wood as you approach the end of your step. This is what’s happening in the boot - though not quite as severe as your plywood shoes. A brand-new boot that’s fresh off the production line is going to have a very stiff outsole. As the sole of the boot breaks in as you first begin to wear them, this heel slippage diminishes and sometimes disappears altogether as it flexes more with your step. Don’t freak out with heel slippage - the boot just needs to break in a bit.

Boot Socks
It’s important when trying on different boots that you’re wearing the right kind of socks. Boot socks are generally

Dan post boot socks

reinforced in the areas where boots tend to wear, and they are thicker, much thicker, than dress socks. You want to make sure you’re wearing the socks that will be on your feet when they’re in your boots, otherwise a properly fitting boot may feel too big and uncomfortable. Over the calf boot socks will also prevent the boot shaft from rubbing against your calf, which bothers a lot of people.  We've tried a lot of different socks over the years, and we highly recommend Dan Post Boot Socks.  They are extremely well reinforced, stay up on your calves and keep your feet dry and comfortable.

Aftermarket Insoles
The technologies inside of boots have come a long way over the decades. There’s a lot of technology in cowboy boots these days, from composite shanks to soft and cushy insoles and lightweight synthetic materials in outsoles and heels to make them lighter. They have come a long way, indeed. One way to improve the comfort of your boots, whether they’re brand new or well worn, is by purchasing a set of aftermarket insoles. Most cowboy boots today have removable insoles and replacing them with cushy gel insoles can make you feel like you’re walking on clouds.  You can take a look at our insoles here.

As you wear your new boots, they will break in. The sole becomes more flexible, reducing the heel slippage. As your feet warm up the leather, it will begin to reshape around and form to your feet. You will become used to the solid, firm foundation that boots give you. In all likelihood, you will begin to love wearing your cowboy boots as much as your favorite jeans. And you’ll start to wonder how you went so long without a pair of cowboy boots.