Feet that Feel Comfortable in a Hurry: Your Quick, FREE and Easy Guide on How Cowboy Boots Should Fit

It’s normal that when you’re wearing a new piece of gear or clothing you might not know how it’s supposed to fit. 

This is more true with cowboy boots than most pieces of clothing or footwear you’ll put on your body.

For this reason, I’m going to take the time today to dive into the specifics of how Cowboy Boots are supposed to fit.

Whether or not you’ve got a pair, or not, this information will serve as a great reference point for the future if you do decide to buy a pair.

How Should Cowboy Boots Fit?

Cowboy boots are supposed to give your feet a firm hug all around. You shouldn’t feel pressure, rather it should be 360 degree support. While putting them on you will feel resistance on your instep and heel, but in properly fitted boots this will disappear when your feet slide into place. 

At the Heel

While putting on your new cowboy boot you should experience some resistance from the boot’s backstay

Just prior to your heel reaching the insole of the boot, just as you think that maybe the boot is too small, you’ll feel your heel slide comfortably into place. 

Your heel should be gripped by the boot, but not pinched; you’re not fighting to get it to land on the insole.

The heel is the most difficult part to fit when buying cowboy boots, as it takes time to break them in to get your final proper fit

Remember mom saying “you’ll grow into it,” it’s definitely true in this case.


It’s okay to have some heel slippage of between ⅛ and ⅜  inch; this is in contrast to the fitting suggestions I wrote about work boots

The reason so much heel slip is okay for new cowboy boots is that the soles are going to be stiff, and as you break them in they will bend.

Once this begins to happen, your boot will bend at the area of your arch instead of your heel slipping out. When boots are new, your feet gives before they do. 

Be patient, that’ll change with time.  

As for the feeling of the heel, as I said above, the boot should encompass but not strangle your heel. 

For anyone that’s played football, lacrosse, ice hockey, or baseball: remember what a proper fitted helmet felt like? 

Shoot for that type of fit and feeling.

For my friends in South Asia and the UK, I’ll throw cricket on that list too. 

At the Toe 

Contrary to what their appearance might lead you to believe, your toes should have plenty of room to move and maneuver in cowboy boots. 

Depending on the design, your toes could have anywhere from ½ inch to 1 ½ inches of open space in the toe box area. 

Ariat cowboy boots usually have a more square toe whereas some other brands may consist of a rounded or pointed toe.

You’ll find a more pointed or snip toe to be more common amongst women’s cowboy boots.

If the boot is crunching the side of your toes then it’s too small. 

At the Instep (Vamp)

Fitting the instep of your boot is the most important aspect as it’s what’s keeping the boot from slipping off as you step. 

You should feel resistance on the top of your foot in this area while pulling the boot on, and a comfortable pressure while wearing; just a slight amount, not a ton.

The instep fitting corresponds with the tongue area on a work boot and isn’t something that everyone has dealt with unless they’ve owned cowboy boots or pull-on boots in the past.

Remember: the pros at getting a good instep fit are immensely patient! Boots, particularly cowboy boots, don’t care which design or brand you wanted. They’re not going to fit just because you want them to.

Take time, explain what you’re feeling to the salesperson, ask questions. If you think it’s going to be possible to run in and out with a new pair of boots in 

Getting the perfect fit at the Ball of your feet 

The ball of your foot should land at the area of the boot where the outsole bends as you step. 

Sometimes this is hard to tell, so bring a friend or your lady (or man, don’t go woke on me now) to help put some eyes on this. 

The sides of your foot should feel contact, but not pressure.

The ball of your foot shouldn’t be crushed on the sides so go a shoe size wider if you have to. 

If the retailer doesn’t have a size wider, go somewhere else. 

Don’t railroad this decision through and get boots that are a narrow width, you’ll be the one that suffers. 

A Good fit at the Ankle

The ankle of your cowboy boots should give firm support to prevent them from rolling. 

If your ankles are bouncing around in the boot, they’re too big. 

Don’t skip this aspect of your fitting, as even if everything else feels good you can injure yourself if the ankles are poorly sized.

Ideally you want them nice and snug.

However, you don’t want them as tight as a rubber band around your ankle. 

You’re not trying to cut off circulation here!

At the Calf

Cowboy boots should be a little loose in the calf area as this is a muscle that flexes as you work; anywhere from ½ inch to 2 inches is okay. 

You also need a little bit of room to navigate your foot into the boot as you’re putting them on so give your calves a break when it comes to fitting!

You’re not wearing boots for the catwalk, you’re wearing them to navigate through the great outdoors. Don’t create a perfect seal that will make you sweat so bad you never want to wear them. 

How Do I Break In My Cowboy Boots? What Do I Do If My Cowboy Boots Are Too Tight?

I’ve got a whole article on this exact topic right here. Check it out if that’s the question you’re trying to answer.

Are Cowboy Boots Supposed to Fit Differently Than Other Footwear?

Cowboy boots are supposed to be more form fitting than regular work boots. Remember that and don’t go into the fitting process expecting the exact same experience you had while purchasing a pair of steel or composite toe boots

How Should Cowboy Boots Feel When You First Buy Them?

Because of their sturdy welt construction, full-grain leather, and design that uses fewer pieces than work boots, expect cowboy boots to feel a little stiff when you first wear them.

How Long Does it Take To Break In Cowboy Boots?

There are a number of answers on this, but it’s safe to say you’ll feel a difference after using them for a week of work. 

Past that point, you’ll really feel like they’re your own after 3-6 months. 

That said, they will continue to get more comfortable as the years go on and fit only your foot. 

How Do You Put a Pair of Cowboy Boots On Properly?

  1. Sit down
  2. Grab the boot by its pull tab or holes and lean it towards you roughly 30 degrees
  3. Point your toe down in, and insert it into the boot and follow the path of the vamp, gradually turning your toe towards the front of the boot before it smashes into the bottom of the insole.
  4. When you feel resistance on your heel and instep press your heel down hard at the same time you’re pulling up on the boot.

My Cowboy Boots are Loose: 5 Steps for a Better Fit

  1. Completely soak the boot in water for an hour
  2. Take it out, empty the boot out.
  3. Soak the type of sock you normally wear and put it on
  4. Put the boot on
  5. Wear it as long as possible or until dry. 

I’m Having Some Difficulties Here, Should My Cowboy Boots be This Hard to Put On?

No, if you’re really struggling to get your cowboy boots on, you’ve got a pair that’s too small. 

There’s a little bit of pressure, but nothing you can’t push through with just a little bit effort. If you’re really tugging and breaking a sweat, get a larger size.