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May 3rd 2022

Cowboy Boot Comfort Tips and Tricks

How to Make Cowboy Boots More Comfortable

If you spend any amount of time wearing cowboy boots, you want to make sure they’re comfortable. But if you’re experiencing pinching, squeezing, or heel discomfort, you may need to make some adjustments for a better fit. Try these seven tips for making sure your cowboy boots are providing the most comfortable fit.

1) Make Sure You Have the Right Size

First thing’s first: Measure your feet to determine your ideal boot size, and try on a few pairs to ensure you get the right fit. Wear boots socks for the most accurate measurement. When determining the best fit, consider:

  • Width: Does a regular width boot provide enough space, or would you be more comfortable in a wide width? If wide widths aren’t available, try on a boot that’s half a size larger and test for comfort.
  • Heel Space: While your boots should offer a snug fit, you’ll want a bit of extra space in the heel. This will allow the boot to conform to your foot for a personalized fit.
  • Toe Shape: Square, wide square, and rounded toe boots offer plenty of space for your toes to spread out. While snip-toe boots look like they’d be cramped, the correct size ensures you have enough room—the boot’s pointed end extends beyond your toes.
  • Manufacturer’s Size Charts: While boot sizes are often comparable between bootmakers, always refer to the size guide provided by the manufacturer to ensure you’re getting a proper fit.

2) Give New Boots Some Time to Break In

Consider where the cowboy boots hurt or cause pressure: If they’re pinching at the sides or tops of your feet, it may be a matter of breaking in the boots—wear them around the house or in the yard to loosen them up and allow them to conform to your specific foot shape. Often, the more you wear them, the better they’ll feel. Sometimes, you may need to take a few extra steps for better comfort, like when the discomfort is mostly in your soles or heels.

3) Add Cushioned Insoles

If a break-in period hasn’t done enough to make your boots more comfortable, and you’ve noticed that the discomfort is in the bottoms of your feet, consider adding some cushioning cowboy boot insoles for a bit of relief. Western footwear insoles are designed to provide cushioning where cowboy boots need it most. Insoles offer many features, including moisture-wicking materials that keep your feet dry and antimicrobial treatments to prevent bacteria and foot odor. Choose from supportive insoles for better stability and gel-cushioned options that reduce pressure in your heels. No matter your specific insole need, there are Western boot insole options to suit.

4) Wear Boot Socks for Better Comfort

Don’t choose just any socks to wear with your Western boots. Cushioned boot socks are padded in all the right places and are tall enough to prevent rubbing at your calves and ankles. Even better, they’re made from moisture-wicking materials and help keep your feet dry, comfortable, and odor-free. For the best performance, choose tall boot socks made from cotton, wool, acrylic, or a blend. If your boots are still in the breaking-in period, you may decide to double-up your socks to help stretch the leather slightly.

5) Get a Professional Opinion

If your boots pinch in specific areas or are only uncomfortable in certain spots, it may be possible to stretch them. To resolve minor discomfort, you may be able to stretch your cowboy boots at home using boot stretch spray and a stretcher—but your best bet is to check with the pros rather than doing this yourself. Shoemakers, bootmakers, and footwear repair shops have the tools and know-how to stretch footwear without damaging the leather as it expands. These locations often have special equipment that uses pressure and heat to stretch boots even more than possible at home.

6) Resole Your Favorite, Well-Worn Cowboy Boots

If you’re not ready to part with your favorite cowboy boots, you can check with the manufacturer or a bootmaker to see about having them resoled. Small cowboy boot repairs, such as sealing cracks or improving water resistance, can be done at home, but these fixes only last a short amount of time. New soles can extend the life of your boots and improve comfort, but if the boots are damaged or causing discomfort otherwise, resoling may not be enough to solve your problems.

7) When All Else Fails, Get New Boots

We get attached to our favorite pair of boots, too, but sometimes an update isn’t such a bad idea. Cowboy boot construction has come a long way in recent years, and new styles are manufactured for better comfort. From the outsoles and insoles to the leather used for the shaft, the latest options in Western footwear are crafted for comfort and stability, day in and day out. When it’s time to find a new pair of trusty cowboy boots, we’re happy to help.


While cowboy boots are purpose-built for the Western way of life, you may need to take a few steps to ensure they’re comfortable while you’re on the ranch, at the jobsite, or out on the town. Follow these suggestions for how to make cowboy boots more comfortable, then explore our other Western Wear tips.