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How Should Cowboy Boots Fit: Hard to Put On? 4 Key Tips

Last updated: November 17, 2023

By: Miles HenryFact Checked

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Are you wondering if cowboy boots should be difficult to put on? The answer is nuanced. While new cowboy boots might feel stiff and challenging at first, this doesn’t necessarily mean they are the wrong size. Properly fitting cowboy boots become easier to put on over time as the leather adapts to your feet.

In this article, we will explore how to determine if your cowboy boots fit correctly and share four essential tips for finding the perfect pair. Remember, a well-fitting boot is key to comfort and ease of wear, so let’s dive into understanding what makes for a good fit in cowboy boots.

picture of a woman struggling to pull on a cowboy boots,

Understanding Cowboy Boot Fit

Cowboy boots, like many types of footwear, have a unique fitting journey that’s important to grasp. To truly understand cowboy boot fit, let’s break it down into three key aspects:

Initial Stiffness of New Cowboy Boots

You might notice they feel stiff when you first lay your hands on a new pair of cowboy boots. This initial stiffness is normal and results from the quality of leather used in crafting these boots. The leather is intentionally firm to structure and support your feet and ankles.

Leather Softens Over Time for a Better Fit

Here’s the exciting part: something magical happens as you wear your new cowboy boots. The leather starts to soften and adapt to the unique shape of your feet. It’s like breaking in a new baseball glove or jeans. The leather becomes more pliable with each step, molding itself to your foot’s contours.

This gradual softening transforms your boots from stiff newcomers into comfortable companions. It’s like a partnership between you and your boots, with the leather getting more accommodating as time passes.

The Difference Between New and Properly Broken-In Boots

Now, let’s distinguish between brand-new cowboy boots and those properly broken in. New boots are often stiff and require a bit of effort to put on. However, this doesn’t mean they don’t fit correctly. It’s just part of the initial process.

On the other hand, properly broken-in cowboy boots are a joy to slip into. The leather has softened and adjusted to your feet, making them easy to put on and exceptionally comfortable. So, don’t be discouraged if your new cowboy boots feel a bit snug at first – they’re just getting ready to become your favorite footwear.

Understanding these nuances of cowboy boot fit will help you appreciate the journey of breaking in your boots and enjoying their perfect fit over time.

Cowboy Boots Shouldn’t be Hard to Put On.

Putting on a pair of cowboy boots can sure feel weird to first-timers. And unless you were careful, you might return the latest pair of boots you bought because they’re too hard to put on. You should try on various sizes and brands when shopping for cowboy boots. By doing this, you get a feel for how different boots fit and should be able to recognize which style and size are best for your feet.

When I was at Cavender’s shopping for boots, I was surprised at the differences in sizes between brands and boot’ styles. Some Ariat boots fit that at size 9, and others at size 10. So, you need to know how the sizes run for the boots you want.

Perhaps one of the most unrealistic things to expect to happen when buying cowboy boots is coming across a perfect-fitting pair on your first try. You have to be patient and choose wisely. And once you’ve bought a pair, you can also try different methods to break in your boots faster.

Most importantly, your boots should only be so tight that your feet are comfortable. My experience with cowboy boots has taught me that a wrong fit can cause pain or leave marks even after you’ve taken the boots off.

Significance of Proper Fit

Now that we’ve delved into the intricacies of cowboy boot fit, it’s time to explore why it matters so much. The significance of a proper fit extends beyond mere aesthetics; it directly impacts your overall comfort and wearability.

Imagine slipping into a pair of cowboy boots that fit you like a glove. Your feet feel snug but not too tight, and there’s no pinching or discomfort. This is what a proper fit achieves: exceptional comfort and wearability.

A well-fitted cowboy boot supports your feet, especially if you plan to spend long hours in them. Whether walking, dancing, or riding, the right fit ensures you can enjoy your activities without discomfort.

Avoiding Discomfort, Blisters, and Foot Strain with the Right Fit

Ill-fitting cowboy boots can quickly lead to discomfort, blisters, and foot strain. Imagine the frustration of a long day with boots that rub against your toes or heels, causing painful blisters. The wrong fit can turn a pleasurable experience into a painful one.

Additionally, wearing boots that don’t fit properly can strain your feet, legs, and even your back. The discomfort can affect your posture and overall well-being. This is why selecting the right size and ensuring a comfortable fit is crucial.

How Poorly Fitting Boots Can Be Hard to Put On

It’s worth noting that the struggle to put on cowboy boots isn’t just limited to new ones. If your boots are poorly fitting from the start, they can always be hard to put on, regardless of how long you’ve had them. This is because the fundamental fit is off, and no amount of breaking-in can fully resolve the issue.

In essence, choosing cowboy boots that fit correctly from the beginning is about comfort and ensuring that you won’t have to wrestle with them whenever you want to wear them.

Understanding the importance of a proper fit in cowboy boots highlights why investing time in finding the right size is well worth it. It ensures that you can enjoy the comfort, style, and ease of wear for which these iconic boots are known.

Picture of me wearing wool socks to ensure my cowboy boots fit.

Key Tips for Finding the Perfect Fit

Now that we’ve established the significance of a proper fit in cowboy boots let’s dive into practical tips to help you find the perfect fit. These tips will guide you through the process, ensuring your cowboy boots feel like they were made just for you.

1. Measuring Your Foot Accurately for Boot Size

The foundation of finding the right cowboy boot fit begins with accurate foot measurements. Here’s how to do it:

  • Use a ruler or a foot-measuring device.
  • Measure both feet because they may be slightly different in size.
  • Measure your feet in the evening when they are slightly larger due to natural swelling.
  • Take note of the length and width of each foot.
  • Consult a size chart from the boot manufacturer to determine your size.

Accurate measurements lay the groundwork for a well-fitted pair of cowboy boots.

Heel slip is pretty basic; it’s the amount your heel slips inside the boot when you take a step. A slippage of approximately half an inch is normal and acceptable.

  • Instep should fit snugly.

There should be minimum space between the instep of your foot and your cowboy boot. However, the instep of your boot shouldn’t be so tight that it makes you uncomfortable.

A firm instep is what gives your foot control of the cowboy boots. The laces’ primary purpose in regular boots is to ensure that the insteps are close-fitting. In contrast, boots with low insteps can make it difficult for you to put them on.

  • Leave some space at the toes.

The space between your toes and the inner tip of your boot affects how easy your foot feels. There should be around 3/4th inch of a gap between the longest toe and the end of the toe box.

I know my boots aren’t too short if I can curl up my toes easily. If there’s an uncomfortable restriction at the toe area, it might be why your feet feel bad in cowboy boots.

picture of a new pair of Justin cowboy boots,
Justin Ropers

2. Understanding Boot Width and Toe Shape Options

Cowboy boots come in various widths and toe shapes to accommodate different foot types and style preferences. Here’s what you need to know:

  • Boot Width: Boots are available in different widths, including narrow, regular, and wide. Choose the width that matches your foot width for optimal comfort.
  • Toe Shapes: Cowboy boots offer a range of toe shapes, such as pointed, rounded, square, and more. Consider both style and comfort when selecting a toe shape.
  • The ball of the foot should be relaxed.

The ball of your foot shouldn’t be pushing too hard against the sides of your boot. It also shouldn’t go so forward that your toes get squeezed in the toe box. A simple rule that a good friend shared with me is that the ball of the foot should align with the ball of the cowboy boot.

Understanding these options lets you narrow your choices and find a boot that suits your feet and style.

3. Tips for Trying on Boots In-Store or Buying Online

Whether you’re trying on boots in a physical store or ordering online, these tips can help:

  • Wear the Right Socks: Always wear the socks you plan to wear with your boots. This ensures an accurate fit.
  • Try Both Feet: Try both boots on and walk around to assess comfort and fit.
  • Online Shopping: If buying online, check the store’s return policy to ensure you can exchange or return boots if they don’t fit.

Properly trying on boots ensures you’re making an informed choice.

4. The Importance of Wearing the Right Socks

Your choice of socks can significantly affect the fit and comfort of your cowboy boots. Here’s why it matters:

  • Choose socks that provide the right level of cushioning and support.
  • Avoid thick, bulky socks if they make the boots feel too tight.
  • Consider moisture-wicking socks to keep your feet dry and comfortable.

Wearing the right socks complements the fit of your boots, enhancing overall comfort.

By following these essential tips, you’ll be well-prepared to find the perfect fit for your cowboy boots, ensuring they look great and feel incredibly comfortable.

Picture of my new Amos Ariat boots.
Ariat “Amos”

What are the Most Comfortable Cowboy Boots?

If you’re like most people, you probably think of cowboy boots as being uncomfortable. We’re here to tell you that’s not always the case. In fact, there are some cowboy boots that are downright comfortable.

In this section, I will share our top picks for the most comfortable cowboy boots on the market today. But one thing I’ve learned by being around people who wear cowboy boots is that every foot is different.

Some of my friends swear by one cowboy boot brand that others complain about. However, I have found that the most comfortable cowboy boots usually fit your feet best. So, trying on a few pairs before making a purchase is essential.

Once you’ve found a pair of boots that fits your feet well, it’s time to focus on the comfort level. Good cowboy boots should be soft and flexible yet still support your foot. And if you’re wearing them all day long, you’ll want to make sure they’re comfortable.

So, without further ado, here are our top picks for the most comfortable cowboy boots on the market today:

Ariat Circuit Patriot Western Boots

Where to buy: Amazon

Customer reviews: Over 2,000 reviewed these boots, and they rated them 4.6 out of 5 stars.

The boots have a unique style, and as with most Ariat boots, they have excellent quality thanks to the Duratred outsole and Advanced Stability Torque technology.

The gel-cushioned footbed and heel stabilizer offer a comforting experience and minimize shock. You’ll appreciate this feature if you have to run in them or if you work in an environment that’s hard on your feet.

It took me a while to warm up to square-toe boots, but now I like the look, and I’ve always been a fan of mid-calf shafts; I find them cooler and more comfortable than boots with tall shafts.

These Ariat boots are good boots for long days working around the barn, look nice enough to wear to town, and make a decent pair of riding boots. The boots are effectively wear-resistant, lightweight, and flexible to support active lifestyles.

Laredo Women’s Miss Kate Western Boot

Customer reviews: 389 customers gave these 4.5 out of 5 stars. See what they have to say.

These decorative women’s boots have a 12 inches long shaft and 1 ¾ inch high heel. The boots pay special attention to Western fashion, using contrasting visuals and a snip-toe design.

More importantly, their pure leather insides and cushioned insoles promise comfort and ease. The boots are also an excellent choice for people with wider feet.

Final Words on How Should Cowboy Boots Fit

The fit of your cowboy boots is not a mere detail; it’s the foundation of your comfort and enjoyment. Here’s a brief recap of why cowboy boot fit matters:

  • A well-fitted cowboy boot ensures overall comfort and wearability.
  • It prevents discomfort, blisters, and foot strain, allowing you to enjoy your activities fully.
  • Choosing the right size and style from the start saves you from struggling to put on poorly fitting boots.

Now that you understand the significance of a proper fit, it’s time to take action. Apply the key tips we’ve discussed to find the perfect cowboy boots for you. Whether measuring your feet, exploring different widths and toe shapes, or trying on boots in-store or online, each step brings you closer to the comfort and style that cowboy boots are known for.

Don’t settle for discomfort or difficulty in putting on your boots. Embrace the knowledge you’ve gained, choose wisely, and step into a world of comfortable, easy-to-wear cowboy boots that perfectly complement your style and stride. Your feet will thank you, and you’ll enjoy every step of the journey.

Below is a helpful YouTube video that provides three keys to ensure you get the proper fitting cowboy boots.

YouTube video

Do cowboy boots hurt at first?

Yes, cowboy boots may feel uncomfortable at first due to their stiffness. New boots need time to soften and mold to your feet. Wearing them gradually and using proper fitting techniques can ease this initial discomfort.

Do cowboy boots loosen up?

Yes, cowboy boots typically loosen up over time as the leather molds to your feet. This natural process improves comfort and ease of wear, making them more comfortable with each use.

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