Most Comfortable Cowboy Boots Buying Guide | Real Experience

Most comfortable cowboy boots buying guide real experience

When it comes to finding the perfect pair of most comfortable cowboy boots, you’ll want something that is well-fitted. This guide will help ensure that your purchase meets all of your needs and doesn’t leave room for regret down the line.

Toe shape

The boot can be pointed with a sharp tip, rounded or square with an artfully narrow top. You may or may not know what style you are looking for when shopping, but most boots have a stay in their shapes that will give you an idea of what you might like best.

Your toe should not be smashed when wearing your most comfortable cowboy boots. When you try them on, you can ask for a minute or two to sit down in the store and give the boots some time to conform to your heel and toes. If you have a friend with you, have them check that your toes are still comfortable after five minutes of walking around the store.

When you are wearing pointy toed boots, your toes should have complete freedom of movement, but not be sitting directly on the front of the boot. The inside edges of your big toe and your pinky toe should not rub together when walking around in your new boots. This means that there is too much space between them. However, the boots need not be uncomfortably small.

There is a difference between tight and uncomfortable, but that’s for you to decide. If you are having trouble deciding with your toes are doing when wearing the boots around in store, take a minute to close your eyes – do you feel too much pressure? Too little? What if you relaxed your foot? Would that help?

If you find a pair of boots that feel good, but something is just a bit off, don’t worry. There are ways to tweak the space. If there’s too little room for your toes between the front of the boot and the pointy toe box, buy some moleskin or gel inserts that have a thicker toe area. You can trim moleskin or gel to fit, but it’s best to buy some that is cut specifically for the boot you are wearing.

Do you find that your toes bump into each other? A little moleskin on the inside of your pinky toe will make life more comfortable.


Width is an important factor, especially if you are buying wide shaft boots. Ask to try on a few different widths of the same boots, as one size may fit differently from another. Be sure that your feet have room to breathe and wiggle around in there. You don’t want them to feel cramped or constricted at all.

If you choose a boot that is too tight and narrow, don’t worry. You can break them in by stuffing them with moleskin or gel to help the inside fit your foot.

Tall vs short shafts

You want your boots to hit at an equal length as your pants. The best way to tell if they are the right height is to have a friend measure from your heel down to the bottom of your knee. This length should match from where the shaft of the boot meets with pants.

If your boots are a bit too tall, they can be worn pulled up a little higher on the leg – this is a popular look with some of the more fashion-forward boot wearers. If they’re too short, have them stretched at a cobbler.


Quality stitching makes for a better boot that will last you a long time. Make sure that the stitching is straight and even, without large gaps or frayed edges.

Look for a boot with a higher stitch count – anything over 100 should be fine. More stitches means a sturdier, better made boot. Boots have their own language when it comes to threading, so if you’re not sure what you’re looking at, make sure to ask a salesperson for help. Your boots will last longer if the stitching is secure and well made.

Boots with laces vs pull on shafts

When trying on pull-on style boots such as ropers and cowboy work boots, make sure to zip them up (or use a strap wrench) since it’s hard to tell if they are comfortable or not when sitting down.

If you have a hard time getting the boots on, then don’t buy them. You should have to use very little effort to get your new boots on quickly and efficiently.

What if I have wide calves?

Even if you have large calves, there are still options for you. You can start by measuring around your calf with a tape measure (make sure the tape is level to get an accurate circumference number). Most brands list their measurements in inches and also in centimeters, so it’s easy to use both systems.


It is important that your boots fit the shape of your feet. After all, you are going to be wearing these boots for 8-10 hours a day – you need them to feel good.

Your boots should have an arch in the sole of the boot (this is especially important if you plan on doing any sort of walking or standing for long periods of time). An arch will make life easier for your feet, and it also helps you balance when riding a horse.

You should also try on your boots with the socks or insoles that you will wear when wearing them. It’s hard to tell if they fit just right with a thin sock, but when you add in your favorite wool socks, it might feel like heaven.

What about the heel?

Your boots should have a good amount of support in the heel and insole. A lot of cowboy boots have 1/2″ heels, which are good for wearing to work or around town. If you plan on owning a horse or riding more often, then get boots with at least one inch heels – this will give you better stability when doing any sort of activity that requires your boots to have some lift or elevation.