Ultimate Guide on How to Wear Your Cowboy Hat Correctly

Cowboy hat trends have never ended even nowadays. For both males and females, a cowboy hat is a good accessory for fashionable dressing.

But for some new starters who want to try the western style, picking and wearing your cowboy hat might be an overwhelming challenge.

As a first-time buyer, you might have no clue how to choose a suitable cowboy hat style for yourself and wonder about how to wear it correctly.

No need to worry. This article aims to help you how to get the right cowboy hat and how to put it on your head properly. Besides, you can also know about some traditional cowboy hat etiquettes.

how to wear a cowboy hat correctly and properly

How to Wear Different Cowboy Hat Styles?

Of course, to wear your cowboy hat correctly, you need to pick out a hat. First, you need to learn about how to choose the cowboy hat style.

In 1985, John B. Stetson create the initial model of modern cowboy hats that is quite ordinary from today’s view. After so many decades, cowboy hats have derived many different styles.

Here’re the main cowboy hat styles.

  • Cattleman
  • Pinch Front
  • Gus
  • Brick
  • Fedora
  • Gambler/Telescope
  • Boss/Boss of the Plains

– Males

For males, to reach the masculine style you need to try cowboy hats that have mid brims and high, angular crowns.

The best style ideas for you are Boss of the Plains, Gus, and Fedora. You can go with any of those styles of your own preference.

– Females

And for females, you will look more attractive with a wide curved brim and creased crown cowboy hat like the classic Cattleman cowboy hat.

The Pinch Front style is highly recommended because cowboy hats in this style can make your face can look thinner.

– Or According to Your Face Shapes

On the other hand, you can choose cowboy hat styles based on your own face shape. A good cowboy hat can modify your face and promote your attractive points.

The rule is simple:

Choose cowboy hats that bring what you lack/offset your excessive part.

Generally, it works as follows:

1. If you have a round face shape or chubby jawlines, you can settle for cowboy hats that have typically creased crowns and sharp brims like Cattleman and Brick style to balance the roundness on your face.

2. Try a Gambler or Boss (of the plains) cowboy hat to soften your facial contour if you have a more angular face.

3. To improve your short face, you can choose a higher crown cowboy hat like the Gus or Tom Mix style to add some length to your face.

4. The Telescope cowboy hat will suit you best if you own a long or oblong face shape. The rather low crown can avoid over elongation of your face.

How Should A Cowboy Hat Fit?

how should your cowboy hat fit your head to wear it correctly

When looking for cowboy hats a suitable size is very important. Unlike ball caps, cowboy hats do not have adjustable closures.

Hence the importance of the right size goes without saying. The cowboy hat should fit your head like this:

  • Fit firmly on your forehead and the back of your head but leave some space on each side.
  • The sweatband should sit 2 fingers above your eyebrows.
  • From the view of the side, your cowboy hats should be set no more than 1 inch below your ears.

In this way, your cowboy hat can snugly fit on your head without causing a headache if you need to wear it for a long time. And the wind won’t blow away your cowboy hat easily.

If you have purchased a cowboy hat that does not fit your head for being too big, there’s a way to fix this issue so you don’t need to buy a smaller one.

You can buy some foam strips and put them in your cowboy hat to make your cowboy hat fit tighter.

First, check your hat and find which part fits loosely, then you can decide whether you need to put the foam all around your hat or just put some in the front or the back of your cowboy hat.

To make the foam stay firmly in your cowboy hat, you can put it under the band inside the hat if it has.

Straw & Felt: When Should Wear These Cowboy Hats?

Most cowboy hats are made from various animals’ fur or straw, even today. Also if you want to get the most classic feeling of the cowboy hat, you should choose these two kinds of materials.

Traditionally a felt cowboy hat is made for warmth while the straw cowboy hat is very breathable and offers cool shade.

Hence you can see that there’s a seasoned choice on which kind of cowboy hat you should wear.

– Seasons

You can wear a thermal felt cowboy hat to defend the cold air from the fall to winter. Or you can name it the “Labor Day felt rule”.

Felt cowboy hats are thermal enough to keep your head away from coldness, and this natural water-resistant can help you with sudden snow or drizzle.

On the other hand, in summer and spring, you can choose a cool straw cowboy hat that can protect you against dazzling sunlight.

Additionally, for the rainy days, a cotton oiled cowboy hat is more proper to wear.

– Occasions

What’s more, the wearing occasion also matters if you want to wear your cowboy hat correctly.

Not only does a well-made, decent felt cowboy hat cost you a lot of budgets, but you should wear it in the formal event, and when you should show your decency.

You can wear your felt cowboy for attending:

  • Weddings
  • Funerals
  • Important meetings
  • The local events

Besides, wearing straw cowboy hats requires fewer rules. You can wear it on daily work or when you take a vacation to the beach or some warm areas.

The best wearing occasion for straw hats will be:

  • Working outside
  • Summer vacation
  • Beach Time
  • Bustles

How to Wear Your Cowboy Hat on Your Head Correctly?

You can wear your cowboy hat in the way you preferred, but here’re some tips to make sure that you are wearing it correctly.

The first basic rule is wearing your cowboy hat with the front to the front.

– How to Find The Back of Your Cowboy Hat

Check the inside of your cowboy hat to find whether there’s a small bow around the headband, which remarks the backside of the hat.

And when you wear your cowboy hat this bow should be at the back of your head.

If your cowboy hat doesn’t have this bow, there’s a trick to tell the front and back: the front of cowboy hats usually are narrower than the back. Then, you can position your cowboy hat by your preference.

– How to Position Your Cowboy Hat

In a traditional and practical way, you can wear your cowboy hat with the sweatband against your forehead.

Your face can get the best sun protection and you will look like a real cowboy or rancher. Pay attention that you will look more serious if you tip down the brim over your eyebrows.

On the other hand, if you want to show your friendly and outgoing, you can slope the brim up above half of your forehead. But your hat can be blown away with the sudden wind.

Slanting your cowboy hat will give you more confidence and people will think you are looking for love or trouble.

How to Wear Your Hair with Cowboy Hats?

Cowboy hats look good on various kinds of haircuts so you can have a try without consideration. One important thing is that make sure your hair won’t bother you to wear your cowboy correctly.

– Short Hair

If you have hair within the length that is not over your shoulders, just let your hair down naturally. Like the Pixie or some simple neck-length hair curved hair.

But if you have a haircut that adds some vertical volume like pompadour or quiff, don’t make your cowboy hat over snugly fit on your head, or it will damage the shape of your haircut.

Or you can use some hairspray to enhance your haircut before wearing your cowboy hat.

– Long Hair

When wearing a cowboy hat make sure to brush your hair back or it may block your sight.

For mid-back length hair, you can make a low ponytail in case the wind mess up your hair.

This works efficiently for those men or women with mid-length curved hair, you can look very stylish when wearing the cowboy hat with a low ponytail.

You can also wear your hair in a braid if you have shoulder-length hair. What’s more, for a western outfit style you can use a bandanna to hold your hair.

– With Bangs

Though bangs are stylish and add a unique charming sense to your appearance, when wearing cowboy hats you need to sweep them to the side and fix them with hairclips.

If you have curved your bangs then when wearing cowboy hats you can tilt the brim a bit up to protect your bang’s shape.

What Can You Wear with Cowboy Hats?

When talking about what to wear with cowboy hats, no one should neglect a pair of cowboy boots. Cowboy hats always match with boots best.

If cowboy hat boots are far beyond your budget you can try a pair of neutral color combat boots or work boots.

The color of boots is better for natural brown or camel. A bit darker color is also a stylish choice.

For the outfit, you can try a button-up shirt in a solid color or with some strips. If the air gets cold you can wear a flannel shirt or a sweater with a jacket.

Blue straight jeans are what you want to match with cowboy hats. Pure blue or navy blue both are neat choices.

How to Wear Your Cowboy Hat While Driving/Riding?

how to wear your cowboy hats for riding

A lot of people choose to wear their cowboy hats while driving to block the sunlight. And cowboy hats are important headwears for riders.

Whether you choose to wear your cowboy hat for driving or riding a horse, you need to keep the cowboy hat firmly on your head for safety.

Otherwise, it will fall off and block your view and that is very dangerous.

Besides choosing the right fit size to let your cowboy hat in place, you can try the following tips on how to make your cowboy hat steady on your head.

– For Driving

If you are driving on the smooth road, your cowboy hat should be worn right in your head with the sweatband right above your eyebrows and the side should be sitting just at your ears.

To handle the rough road, you need some method to keep your cowboy hat steady on your head.

  • Put some weather stripping inside the band of your cowboy hat to use to make your cowboy fit snugly.
  • Clip bobby pins on your hair and insert them into the band of your cowboy hat.

– For riding

Also, you need to keep your cowboy hat in place while riding. Sometimes riding on a horse is much bumpier than driving a car.

For riders, you can tighten the chin cord or use a bandana to tie your cowboy hat in. Then adjust your hat brim facing downwards to against the wind.

About Cowboy Hat Etiquettes

As the staple of western style, cowboy hats have blended into the traditional culture in many locations. If you want to wear your cowboy hat to attend some events, be sure to memorize some etiquette to show your respect.

– When Should Cowboy Hat On & Off

Most time you can keep your cowboy hat on when outside to protect you from the sun. But here are some public situations you need to take off your hat as a sign of respect.

  • When you meet someone (especially an elder one) for the first time
  • While attending a funeral
  • In the Pledge of Allegiance (Put it on your heart)
  • In presence of the flag

Besides, remember to take off your cowboy hats while going into buildings or restaurants. But on some informal occasions, you can keep your hats on. Here’re the indoor occasions you should take off your cowboy hat.

  • Indoor weddings/funerals
  • In church
  • At the table(you can keep it if you are eating an informal dinner at a counter)
  • Into other people’s homes as a visitor


1. Is it ok to wear a felt cowboy hat in the summer?

Not Suggested. Felt cowboy hats are made for warmth to help cowboys defend against cold wind and snow. For summertime, you can wear a breathable straw cowboy hat to protect your face from sunlight.

2. Can you wear cowboy hats with sneakers?

Not suggested. Though can try a pair of ankle sneakers in solid khaki or brown color, which should look less incoordinate. Just a pair of work or combat boots go much better with cowboy hats.

3. Can you wear cowboy hats with shirts?

Yes. When wearing cowboy hats you can wear a cool causal outfit style with solid or stripe shirts.

4. What does it mean when a cowboy tipped his hat?

It means a kind of non-verbal greeting action between friends or acquaintances while meeting on the street or at a gathering. Try with your pals next time!

5. Why Do Cowboys Wear Hats?

For warmth, cool shade, and protection against the elements. Cowboys also use cowboy hats to inform other riders on the horse. Everyone should try a cowboy hat for one time.

6. What does a black cowboy hat mean?

There’s no special meaning of cowboy hat colors. But for the summer, You may feel very hot with a black cowboy hat since it absorbs more heat than other color cowboy hats.