Cool Cowboy Hats that Quentin Tarantino, Kid Rock and Alex Oliveira are Wearing

mens cowboy hats

Chris Dickinson is a cowboy rancher, digital artist and Instagram influencer who knows cool cowboy hats. And he says some styles of men’s cowboy hats make a statement about what kind of cowboy you are. 

Admit it. After you saw the Brad Pitt cowboy hat he wore as Tristan in Legend of the Falls, you wanted one too.

Quentin Tarantino in a Black Felt Men\'s Cowboy Hat.
VENICE, ITALY – SEPTEMBER 03: Director Quentin Tarantino gets his Lifetime Achievement award at the 67th Venice Film Festival in a gambler style men’s felt hat. (Photo by Pascal Le Segretain/Getty Images)

From dressing up as cowboys for Halloween to watching old-time, country western reruns, Americans have and love the cowboy mystique.

We idolize TV characters such as Walker Texas Ranger.

We’re enamored with actors like Clint Eastwood and John Wayne. Their fictional cowboy personalities reflect the true essence of western culture and their values, which we strive to embody. 

Gucci cowboy hats are even a thing now.

Robert Rodriguez in a felt men\'s gambler style cowboy hat.
VENICE, ITALY – SEPTEMBER 01: Director Robert Rodriguez at \”Machete\” premiere at the 67th Venice Film Festival. (Photo by Gareth Cattermole/Getty Images)

A cool cowboy hat reminds us of integrity, strength, freedom and fearlessness. A cowboy is the original outlaw, the bad boy with a sense of pride and virtue.

It’s no wonder the fashion world is embracing this longtime country accessory, and we’re seeing it in the closet of American city slickers.

Alex Oliveira in a Brazilian style straw cowboy hat with black and white hat band.
LAS VEGAS, NEVADA – OCTOBER 01: Alex \’Cowboy\’ Oliveira of Brazil at UFC Fight Night weigh-in. (Photo by Jeff Bottari/Zuffa LLC via Getty Images)

If you’re new to the cowboy hat scene, here’s the types of cowboy hats you need to know about to bring out your inner cowboy. 

Find Your Inner Cowboy

Chris Dickinson is a rancher and digital artist Instagram influencer. He has gained 70,000 followers by sharing visuals of the day in the life of western cowboys. Images on his feed showcase everything from roping to branding, and feature shotguns and horses against the backdrop of Utah’s bucolic mountain ranges. 

He says being a cowboy isn’t a lifestyle – it’s what’s inside of you. 

“You might be somebody who lives in New York City in a high-rise building, but be a cowboy at heart. You may have never put boots on or a cowboy hat on before, but that doesn’t mean you can’t wear it.”

Types of Cool Cowboy Hats

As with most fashion statements, the type of men’s cowboy hat you wear says a lot about who you are. 

“For example, when you see a flat crown, which we call a gambler, which is identified as a cowboy hat with a flat brim with a tiny curl on it, you’re sending the message that you are a buckaroo,” he said. 

Moms and kids cowboy hats are a longtime style for country people and rodeo lovers.
Miss Nevada High School Rodeo sport traditional, cattleman style cowboy hat. Pictured from left to right is Jenni Mann, Josie Linberg and Jaxson Kidd. (Photo by David Becker/Getty Images for Professional Bull Riders).

“If you see somebody wearing that kind of hat, you know they follow the same cowboy code. But their tools are a little different,” he said. 

What kind of men’s cowboy hats are out there, and what do they say about you?

That depends on who you ask. Meg Gallagaher, an LA-based stylist who also loves cowboy boots, says while we often associate the men’s cowboy hat with places like Texas or in the American south, or think of the ranchers and ropers of the west, it’s now becoming quite normal to simply see the hat on those that “want to express themselves individually.” And there are several ways you can do this, as well.

Men’s Leather, Felt, and Straw Cowboy Hats

There are plenty of men’s cowboy hats to choose from which are not necessarily just for men. J.Lo worn a distressed leather cowboy hat to the Met Gala this year. 

For starters, there’s the traditional crown, cattleman’s hat known for having a slight bend in the brim. Then there’s the flat cowboy hat associated with the vaquero days.

Vaqueros, a Spanish word for herders of cattle, were said to be the originators of the North American cowboys when they came from Spain and eventually to the Americas as cattle farmers. 

Then there’s the gus-style men’s cowboy hat, the mark of Montana cowboys. They’re also called “lonesome dove” hats with a curled brim, deep crease, symmetrical pinch and tall crown.

Country star Jason Aldean in a straw cowboy hat on stage
Country star Jason Aldean sports a gus-style cowboy hat during his live concert at the Park Theater at Park MGM on Dec. 6, 2019 in Las Vegas (Photo by David Becker/Getty Images).

The naked cowboy would almost be naked if it wasn\'t for his cowboy hat

The Naked Cowboy officially changes his underwear to Fruit of the Loom\’s new Boxer Briefs at Times Square. (Photo by Craig Barritt/Getty Images for Fruit of the Loom)

There’s also the straw cowboy hats that traditional cowboys wear during the summer months but in the fashion world tend to be up for grabs in terms of when to wear them and why. Associated with country stars and musicians around the nation, they tend to make the statement of fun, light, and free. 

Matt Salazarlla in a straw cowboy hat with a beaded hat band.
Rock and roller Matt Salazarlla sports a beaded straw cowboy hat during an event at the Village Studios in LA. (Photo by Rick Diamond/Wireimage).

And then there are the leather cowboy hats, which Dickinson says you don’t see in real-life cowboys often. Perhaps you wouldn’t see it out on the farm because they’re heavy and dense, but they do go well with a nice pair of denim or, dare we say, overalls. 

Herbert Coward in a Mens Leather Cowboy Hat with Coveralls
This unique, customized leather cowboy hat suits Herbert ‘Cowboy’ Coward’s denim overalls quite well. The Hillbilly Blood panel during an event at the Beverly Hilton Hotel. (Photo by Frederick M. Brown/ Getty Images).

And the best thing about cowboy hats – you can accessorize them with as well. It’s not uncommon to see cowboy hats with signature ribbons, beads, string or leather hat bands attached to them.

Cowboy Hat Material

Dickinson says it’s not unusual for cowboys to spend thousands of dollars on a hat so when it comes to material, don’t cut corners. 

“The working cowboy gladly spends thousands on a saddle and a hat. At the same time, he has holes in his jeans and boots,” he said. 

Materials come in all colors and quality. Felt men’s cowboy hats, for instance, come in three kinds – rabbit, a mix of rabbit and beaver, or full on beaver felt.

Beaver is the higher-end of this material, but worth the investment as it’s stronger and more durable. 

Kid rock in a felt cowboy hats with a feather hat band.
Felt hats, like this one on Musician Kid Rock, who\’s wearing a gus-style cowboy, make a nice accessory for nights out on the town. Rock is pictured during the 35th Annual People’s Choice Awards in LA. (Photo by Michael Buckner/Getty Images for PCA).

mens stetson cowboy hat
Clark Gable in classic grey felt Stetson cowboy hat with Marilyn Monroe in 1961 publicity photo. (Getty Images)
Clint Eastwood loved to sport the cowboy hats in the older movies
This pale-rider style cowboy hat is a reference to a spaghetti western produced and directed by Clint Eastwood. Today it would be called a gambler-style cowboy hat and is associated with the buckaroo lifestyle. Clint Eastwood photographed in 1962 on the set of ‘Rawhide’ (Photo by CBS/Getty Images)

The Hat Stops Here

So whatever our battle may be, you can harness the steadfastness of a cowboy with the right men’s cowboy hats. 

“Being a cowboy is a set of values” says Dickson.

“It’s a way of life in the way that you treat other people. It’s in the way you treat your family and care for your land. It’s in your word and in how you live your day-to-day life,” he said. 

So maybe we can all follow this advice, and bring out our inner cowboy with the right men’s cowboy hat today. 

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