It is not the most conventional, but a cowboy hat is definitely a great addition to your wardrobe. The real trick lies actually learning how to wear a cowboy hat correctly. If you don’t wear it the right way, it could lead to a bunch of problems. Your hat might not fit you properly or even cause irritation on your scalp.
In some rare cases, the size of the cowboy hat might not fit your head and be tight on the sides. This could lead to complaints about pain being caused in those areas of your face. The solution is simple.
Go through this article and learn the do’s and don’ts of wearing a cowboy hat. Let’s dive right into it!

Why Does a New Cowboy Hat Hurt On Side of Head?

Making a cowboy hat is no laughing matter. It’s an art that was perfected over generations. Its origin dates back to the Wild‌ West. Cowboy hats are usually made from materials like leather and felt. It is through these strong materials that a cowboy hat will remain durable in the long run.
However, these materials do come with their own set of issues. The most common one is that the hat feels tight on the sides while feeling perfectly fine in the front and back. There are a bunch of reasons why this could happen. We’ve listed them below:

Shape of your head:

 Everyone has a different shape head. The fact is, that cowboy hats are made for oval head shapes. People whose heads are the right size wear their cowboy hats with no issues. It’s round-headed folks who seem to experience discomfort as a result of these pressure points developing on the sides of their head.

New hat stiffness:

You’ll also find your cowboy hat pretty stiff when you get one for the first time. It’s a natural result of using leather or felt for the material that goes into its manufacture, as noted above. In the course of time, the hat molds into the shape of your head. After some time, your hat will fit just perfectly.

Improper sizing:

This is probably the most important part of buying a cowboy hat. It’s essential that you choose a hat that is actually your size. If you make the mistake of buying a cowboy hat that is even half a size smaller, you’ll notice how it fits comfortably all over your head except for the sides. 

So, how should a cowboy hat fit?

If you’re planning on making cowboy hats a permanent part of your wardrobe, there are a few things to keep in mind. We’ve listed them down below:

Snug but not tight:

The thing you are looking out for here is whether the hat hurts the sides of your head. Does a new cowboy hat hurt on the side of your head? It needs to fit snugly and be able to stay in place. If you start to see that the hat is comfortable on the front and the back but hurts the sides, then it’s your signal to go up a size. Alternatively, get an even more oval-shaped hat.

No gaps:

An important thing to remember is that there shouldn’t be any gaps between your head and your hat. Even the tiniest of gaps could end up ruining your look. Even worse, it risks your hat flying straight off your head. Remember, the key is to buy a cowboy hat that fits snugly from both the front, back, and sides.

Test the fit:

Now, there’s a small test you can carry out to test whether your hat fits you correctly. Put your cowboy hat on and tilt it forward. Now, you’re going to feel a slight bit of resistance. That part’s fine. The key here is to watch out for any reddish marks on the back of your head, or any discomfort.

How to wear a cowboy hat for comfort and style?

A cowboy hat doesn’t just make you look good, it also makes you feel good. You’ll get an instant confidence boost after pulling off such a bold fashion statement. The key is to create a balance between style and comfort:

Positioning:

How should a cowboy hat fit? The proper way to wear a cowboy hat is simple. A rule of thumb is to make sure the front of cowboy hat is just an inch above your eyebrows. The hat should also rest evenly all around your head. It’s not good to pull your hat forward too much. That could end up causing discomfort.

Break it in:

A pair of shoes also have to be allowed time to “break-in,” but so do cowboy hats. You can just start wearing it a lot during the first week when you buy your cowboy hat. Then it will eventually form around the shape of your head. Alternatively, steam is usually applied to toughen the leather up, softening it at some parts, especially around the face of the wearer, and to assist with breaking-in processes.

Adjust with inserts:

If your hat still feels a bit off and isn’t fitting as snugly as it should, don’t worry, we’ve got another solution. You could always use foam inserts. Whichever areas of the hat feels like their loose, just put a foam insert in there. It’ll help your cowboy hat fit perfectly onto your head.

Choose the right material:

 This is a really important part of buying a cowboy hat. Different materials act differently in the long run. An example is felt, which can be a more forgiving material. Over time, you’ll see how it adjusts to the size of your head. On the other hand, materials like straw are more rigid in nature. In the long run, straw hats will probably change next to nothing in terms of adjusting in shape.
How to wear a cowboy hat and make it feel comfortable all day comes down to finding the right fit material.

How can you deal with tightness on the sides of the hat?

Stretch the hat:

You don’t have to do everything by hand. There are tools out there like a hat stretcher that can make your life easier. Just place the hat stretcher inside the hat and turn the knob. Doing this often will shape your hat faster.

Steam treatment:

A common trick to dealing with fitting issues is using steam to widen the shape of your hat. Just hold your hat over some steam and gently tug on the insides of your hat. This will soften the material and allow it to stretch before it gets hard again. It’s important not to overdo this, though. That’s because it could end up damaging your hat’s material.

Professional adjustment:

If you get tired of trying to be a one-man miracle worker and re-size all by yourself, you can always leave it to the pros. Most shops that sell these hats also offer professional resizing services. In fact, they have the tools and expertise to get your resizing done faster and more efficiently than if you took a crack at it at home.

Wear it often:

This is probably the easiest piece of advice we could give you. The more you wear your hat, the faster it’ll adjust to your head size. This is probably the most hassle-free way of getting your hat to fit better out there!

Lets Wrap up

How to choose a cowboy hat that fits well? From the start can prevent some of these issues. But if you experience any discomfort, like does a new cowboy hat hurt on the side of your head, use these tips or read our more exclusive blogs to get the perfect fit.
You would probably be more excited to go out and buy your very first cowboy hat, but before you do so, remember all the tips we’ve outlined throughout this blog. Follow our lead and enjoy your cowboy hat to its fullest potential.
The best source to buy cowboy hats and establish an excellent fitting choice is State of Gracie. Their inventory features a diverse selection that provides plenty of options for customers to choose from.