Apparel FAQ Tips

How to Wear a Cowboy Hat Without Looking Ridiculous

silhouette of cowboy wearing cowboy hat on horse
Written by Holly N.

A Rookie’s “How To Hat” Guide

The appeal of cowboy hats runs deep in American culture. But, if you’re new to Western attire (as I was), you’re probably worried about doing something ‘wrong’ and looking silly. A cowboy hat can add some Western flair to your outfit, or simply provide protection from the elements. But how you wear it depends on your individual style and lifestyle.

If you’re working on a ranch, a cowboy hat is a functional piece of equipment, but if you’re headed to a Western-themed wedding, it can help you both fit in and stand out. Functional yet stylish, a cowboy hat can be worn with everything from jeans to a floral-print dress. Dress it up for the races, or dress it down for a day on the ranch, either way, it will keep you feeling and looking cool— especially if you follow these helpful tips.

two people wearing cowboy hats

Source: Canva

Cowboy Hats 101

John Batterson Stetson is credited with creating the cowboy hat in 1865, when he manufactured the open-crowned Boss of the Plains hat.

Made from beaver fur felt, the Boss of the Plains had a high crown to insulate the head and wide brim to protect the wearer from the sun.

It was much more than a simple piece of headgear, however, and could also be filled with water, used to fan the flames of a reluctant campfire, or waved to get the attention of distant riders.

The cowboy hat is a classic example of form fitting function, and as a result, the construction and design have changed little over the years. Different creases and brim shapes evolved over time, with different ranches developing different looks to distinguish themselves from others.

Anatomy of a Cowboy Hat

  • Crown – the dome-shaped part of the hat that fits over your head
  • Crease – the indentation in the center of the crown that gives it style and shape
  • Dent – the notch on either side of the crease
  • Brim – the overhanging section of the hat that provides shade
  • Front Dip – the center of the brim that dips down towards the face
  • Hatband – the band that fits around the crown, just above the brim
  • Buckle Set – the buckle decoration on the hatband
  • Roll – the curl of the brim

How to Wear

The best way to wear a cowboy hat is… the right way round!

And yes, there is a front and a back to the hat!

If there’s a buckle set or feather decoration, it should sit to the left. Some cowboy hats also have a small bow inside the hatband, which should be worn at the back of your head.

man with glasses and cowboy hat

Source: Canva

Most cowboy hats are narrower at the front, so if it feels too loose around your forehead, you might have it on back to front!

A well-fitting cowboy hat should be snug at the front and back but allow a little space on either side.

You should be able to fit one finger between the hat and forehead, and it should sit level and not tilt to either side.

A correctly fitting cowboy hat should rest comfortably above your eyes and not sit too high on your forehead. That way, it will provide optimum shade without obstructing your vision.

Tips to Look Like a Pro in Your Cowboy Hat

Shaping Get your hat professionally shaped for the perfect look
Care & Storage Keep your hat clean and store it properly to maintain its shape
Seasons Put your straw hat away once summer is over
Short Hair Keep your hair tidy and simple, and let the hat do the talking
Long Hair Wear your hair down or in a low ponytail or bun
When Driving Store your hat, don’t try to wear it!
When Indoors Take your hat off when indoors, removing it using the crown and placing it carefully crown-side down

Common Cowboy Hat Materials

From durable felt to breathable straw, the materials your hat is made from dictates when and where to wear it.

  • Felt — Hats made from felt can be worn year-round. They will be warmer than a straw hat, so may be best in spring or fall/winter months.
  • Straw — These hats are for summer wear, as they are lighter and cooler.
  • Leather — While leather offers excellent protection against the sun, it’s not as breathable as straw or as easy to shape as felt.

Reasons to Wear a Cowboy Hat

Cultural significance and practical purposes are often why people choose to don cowboy hats, but here are a few additional reasons cowboy hats are so popular.

  • To shade your head and neck when working in the sun all day
  • For protection against the wind and rain
  • If you’re going on a long trail ride and might need to improvise a bucket
  • When you’re showing in a Western class at a horse show
  • If you’re attending a Western-themed event such as a concert or rodeo
  • At a barn or country-themed wedding
  • If you’re looking to add some Western flair to an outfit
cowboy hats as wedding attire

Source: Canva

Cowboy Hat Etiquette

Did you know you should never place a cowboy hat on a bed because it brings bad luck? This is just one of several rules governing how cowboy hats are worn and how they should be treated when removed.

For instance, although you should remove a cowboy hat when indoors, it’s fine to wear one in a lobby or elevator. For more facts like these, check out this article on Cowboy Hat Colors & Etiquette for Beginners.

Frequently Asked Questions

Q: What is the right way for a cowboy hat?

The narrowest part of the cowboy hat should be at the front, with the buckle or decoration on the left.

Q: Should a cowboy hat be tight on your head?

A cowboy hat should fit snugly enough that it won’t get blown off by the wind but not so tight that it gives you a headache! The general rule of thumb (or finger) is that you should be able to slip one finger between the brim and your forehead.

Q: Do cowboy hats shape to your head?

Regardless of what material it’s made from, a cowboy hat will gradually mold to the shape of your head. A cowboy hat needs breaking in, much like a pair of cowboy boots!

Q: Which side is the front of a cowboy hat?

The front dip should be front and center.

Q: How do you wear a cowboy hat with short hair?

Keep short hair simple and neat and let your cowboy hat shine.

Q: How to wear a cowboy hat casually?

Pair your cowboy hat with a pair of distressed jeans and a basic tee for the ultimate casual look.

Q: How do you wear a cowboy hat with string?

A stampede string goes under your chin to secure your hat to your head. It means you won’t lose your hat in strong winds.

Q: How do you wear a cowboy hat while driving?

While wearing your cowboy hat when driving isn’t recommended, many people do it. To ensure the safety of everybody on the road, make sure the brim sits comfortably above your eyes so it doesn’t obscure your vision.

cowboy with horse and dog

Source: Canva

Parting Thoughts

You can wear a cowboy hat pretty much any way you want and with almost any outfit. A straw cowboy hat is the perfect accessory for a summer dress and cowboy boot get-up and protects you from the hot sun while working outside.

Felt and leather cowboy hats are great for a day at the races or to wear to a Western-themed event. They’re also resilient enough to wear when working, providing both shade and warmth on those chilly winter mornings.

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About the author


I am Holly, an equestrian enthusiast whose journey with horses began at the age of six in the UK. I've ventured from competing in various local events such as showjumping, cross country, showing, and gymkhana to a more serene but equally enthralling role in South Africa. Presently, I reside and ride in the breathtaking landscapes of South Africa, employed as a trail guide at Wild Coast Horseback Adventures.