How to Properly Fit and Wear a Cowboy Hat: Choosing The Right Hat For You

How to pick a cowboy hat for your face

Have you struggled to find a cowboy hat that you like? It may be because you haven’t found the right one for your face. While some get more light than others, cowboy hats come in many shapes, sizes and materials. This means that regardless of what shape or size your face is, there is a cowboy hat style that will flatter it. Before you dive into a rabbit hole of colors and materials, the first step to picking the perfect cowboy hat is finding out what your face shape is. Then, pick a cowboy hat for your face that flatters your unique shape.

Best cowboy hat for a round face

Those with a round face will want to choose a cowboy hat that has a higher crown and slanted brim. This will make your face look thinner and flatter your full cheeks. Pick a cowboy hat style that has a less rounded brim and a creased crown, like theJasper Raffia Western Hat.

The ideal cowboy hat for an oval face

Lucky you! Those with an oval face shape can pull off just about any shape or size of cowboy hat. We’d still suggest sticking with a medium sized or larger brim, and then choosing the specific style that best fits your personality and hat usage. Start bybrowsing all cowboy hat styles to find one you like! 

Pick this cowboy hat if you have a square face

If you’re trying to determine how to pick a cowboy hat for a square face, begin by looking for styles that feature soft lines. This will balance out the sharper features of your face, and highlight your cheekbones. Consider styles with a rounded crown and brim, such as the Arizona Wool Gambler.

Choose a cowboy hat like this for a diamond face

Diamond faces will want to be wary of cowboy hats that cast a shadow, so pick a hat that’s angular, but doesn’t have a brim that dips in the front. Cowboy hats like theOutlaw Hat are a good choice. Use the shapeable brim to find a style that’s shadow-free, then wear the hat slightly further back on your head to add some width to your forehead area.

How is a cowboy hat supposed to fit? It comes down to the right sizing

One you’ve determined how to pick a cowboy hat for your face, it’s time for the next important step: learning how a cowboy hat is supposed to fit. This is essential for comfort, style, and usability. If your cowboy hat fits too tight, you’ll quickly get a headache, look “squeezed” into your hat, and be left with a forehead crease when you take it off. But if your cowboy hat is fit too loosely, it’ll easily fly off or spin around, and look like it’s much too large for your head. The perfectly fitting cowboy hat will be snug around the front and back of your head, and a little looser around the sides. You should be able to easily take off and put on your hat, but your cowboy hat shouldn’t easily blow away in a small breeze. A good rule of thumb when you’re wondering “how is a cowboy hat supposed to fit?” is to check the fit with your finger. If you can slide one finger between your head and the cowboy hat, it’s fitted correctly.

Measuring your head for a cowboy hat that fits

Most companies have a size chart that you can follow to determine your cowboy hat size. To properly measure your head, use a soft tape measure. Measure around the widest part of your head, which is usually found by measuring about two finger widths above your eyebrows. Then, look at the company size chart to find your perfect size. Yes- even if you’ve bought a cowboy hat that fits perfectly before! Sizing can differ from company to company, so make sure to check before you buy.

Simple Etiquette: The proper way to wear a cowboy hat

Once you have your hat in hand, you may be concerned with the proper way to wear a cowboy hat. Truthfully, many of the rules associated with wearing cowboy hats have become a thing of the past, particularly in less formal situations. But a few general tips on the proper way to wear a cowboy hat will help you feel comfortable in any situation.

Before all else, make sure that your cowboy hat fits your head and face shape properly. This will make you look and feel good. A well-fitting cowboy hat will always look best, no matter the situation.

When it’s time to take off your hat, you’ll want to be careful not to damage it. This is particularly important when it comes to styles made of straw or raffia. Traditionally, it was taught that you always grasp your cowboy hat by the sides of the crown to remove it. Others will tell you to remove it by holding the crown. What is really important is to ensure that you’re careful not to dig your fingers into the hat when you take it off. This will weaken your hat over time and can lead to rips, tears, or creases in the material. The best way to store a cowboy hat is by placing it on a hat rack. If you don’t have a hat rack available, place your hat upside down on a clean, flat surface. Always rest the weight of your hat on the crown. Storing your cowboy hat brim-down will cause it it flatten and lose its shape.

When to take off your cowboy hat

A big part of properly wearing your cowboy hat is knowing when not to wear it. Again, many of these formalities have shifted over the years, but are still practiced in some places. In general, prepare to remove your cowboy hat at formal indoor events, when a national anthem or song is playing, and when you are enjoying a meal. Some people also suggest that cowboy hats are removed when you meet or greet others. But this is a more proper rule that is often no longer followed.

Originally, it was said that straw or raffia cowboy hats could be worn from Memorial Day to Labor Day, and then they should be stored for the cooler weather. In their place, wool or leather hats should be worn. That rule is rarely followed now. Instead, choose the cowboy hat material that feels best suited for the weather you are in.

Did this guide help you determine how to pick a cowboy hat for your face? Now that you know the proper way to wear a cowboy hat, it’s time to choose one that fits you perfectly!

Shop our most popular mens cowboy hat style:The Dakota Shapeable Wool Hat

Ladies, try our most popular women's cowboy hat style:The Navajo Bead and Feather Hat