How to Wear a Cowboy Hat Styles with Wrangler Revelry

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The proper way to learn how to wear a men’s cowboy hat (if cowboy hats can be considered proper) is no longer out on the range. By wearing a pragmatic brand of patriotism much subtler than American flag themed clothing, a-listers are taking victory laps on the world stage wearing different types of cowboy hats.

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Caption: The Searchers, poster, John Wayne on poster art, 1956. (Photo by LMPC via Getty Images) 

From the taupe 10-gallon cattleman cowboy hat that billionaire Jeff Bezos wore on his return from outer space, to Olympic champ Simone Biles, to the pink cowboy hat Lil Nas X wore to the Grammys, major mavericks are borrowing from the symbolism of the old west to brand their wins American. 

In the classic western movie The Searchers, John Wayne plays an aging civil war vet who rides into the sunset after single handedly rescuing his abducted niece in a trademark Stetson. 

His look defines what ultimately became that of the quintessential American hero, marching to the beat of his own drum, and never hanging around long enough to hear anyone say thank you. Instead, he saddles up and rides back out onto the range, all by his lonesome, to right more wrongs.

If you want to borrow some range equity from this legendary hat style and find your inner John Wayne, here are three A-list influencers demonstrating when and how to wear a cowboy hat.

This is what we call the cowboy hat trick. 


1. The Bezos Jetson Stetson 

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Jeff Bezos speaks about his Blue Origin New Shepard space flight. (Photo by Joe Raedle/Getty Images)

Here’s space cowboy Jeff Bezos at the landing of his Blue Origin New Shepard space flight talking about how thin our atmosphere really is when viewed from space, wearing a classic Stetson Boss of the Plains style cowboy hat style reminiscent of John Wayne in The Undefeated. His hat wasn’t nearly as distinctive as the tear drop crown, pure beaver felt Brad Pitt cowboy hat in Legend of the Falls, at least it was common enough to get on Amazon.

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DURANGO, MEXICO – 1969: John Wayne on the set of ‘The Undefeated’ in 1969 in Durango, Mexico. (Photo by Michael Ochs Archives/Getty Images)

Bezos’s better half, Lauren Sanchez rode shotgun in a glam cowgirl ensemble comprised of a $2,600 white Oscar de la Renta minidress, calf-high cowboy boots, a matching womens cowboy hat, tennis bracelet and a $17,500 diamond encrusted Rolex (on her left wrist) according to Daily Mail. She looks almost as good as J.Lo did in her leather cowboy hat at the Met Gala.


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Lauren Sanchez listens as her boyfriend Jeff Bezos talk about his flight on Blue Origin’s New Shepard. (Photo by Joe Raedle/Getty Images)

Sanchez and Bezos both cashed in on the cultural, historical, or aesthetic significance of the moment, chalking up a much needed win for team USA. If he can wear a Jetson Stetson on a rocket ship, we are confident you can figure out how to wear a cowboy hat while driving, or riding a motorcycle for that matter.

Why It Works 

Equal parts NASA astronaut and ranch hand make the Bezos ensemble distinctly American maverick. We’ve always been as fascinated with the possibilities of space exploration as we are with the legend of cowboy, his moral compass baked into his DNA, ready to do what’s right for the sake of freedom, fairness, and justice. 

Granted, it’s a fable based more on aesthetic than fact. Ask native Americans how they feel about the cowboys who settled the west and they’ll give you a completely different set of adjectives. But in these uncertain times, gussying up your image with a little folklore and myth is one way to present yourself and your country as competent, capable, and courageous.

How to Wear It

Bezos wore el jefe aviator shades, a felt men’s cowboy hat, a quasi-military NASA-blue jumpsuit and dusty leather boots to his space landing. Whether you’re settling the great plains, intergalactic frontiers, or lionizing your boyfriend’s suborbital space flight, it’s the classic cowboy hat we see sitting a top a-list heads, looking more Ralph Lauren than rodeo. 

Cop the look by matching a cream brimmed hat with a pair of wire-frame, mirrored Ray Bans and a low pair of suede or leather mid-calf cowboy boots. Finish the ensemble with a bold-colored sporty short jumpsuit (Jeff’s look) or a white summer dress (Lauren’s look).

2. Dream Team Theme

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The US Gymnastics Championships on June 6, 2021, in Fort Worth, TX. (Greg Nelson/Sports Illustrated via Getty Images) 

No hat style makes America chic again more than a traditional cattlemen crease cowboy hat.

Women’s cowboy hats aren’t just for starry-eyed girlfriends cheering on billionaire boyfriends. They’re also for Olympic Champions who in this case performed better under pressure than any other nation on the planet, during what is arguably the most challenging of all times since the Spanish Flu. 

The US Women’s Gymnastics team took a brief respite to acknowledge this win before riding off to compete in other battles. Most US Olympic athletes come from the American heartland. Of the nearly 20 senior members of the team, only 2 of them hail from the coasts. In the heartland, trucker hats are as common as bucket hats are on the coasts. But when the world was watching, these champions hailing from 12 different US states all came together and wore cowboys hats to celebrate and distinguish their win as an American accomplishment.

Why It Works

The women’s cowboy hats worn by the US Women’s Gymnastics Team lend a crisp, clean and calming effect on a already busy patterns of their leotards, and the reptilian print is fresh, sexy and apropos to the cowgirl look. Sunisa Lee’s sparkly magnetic eyelashes bring out the same cowgirl glam look Sanchez wore, sans the diamond encrusted Rolex.

How To Wear It

The pulled back hair is a lesson in how to cowboy wear a cowboy hat with long hair. Pull it back in a super tight bun like a military gal or a cop and maintain your sense of authority while you lift off your cowboy hat, and not a single hair out of place.


3. Gender Bender Surrender

Lil Nas X, awarded Best Music Video and Best Pop Duo/Group Performance for “Old Town Road (feat. Billy Ray Cyrus)” and Album of the Year at the 62nd Annual GRAMMY Awards. (Photo by Steve Granitz/WireImage)

Self-professed Nicki Minaj Barbz boy Lil Nas X, seen here after trading in his guns for Grammys, cut his influencer teeth by sharing yeehaw culture posts online that built his initial social media following.

His first big hit Old Town Road, socially engineered to meme status on Reddit (at least partly) through sock puppetting, went from the country to pop charts with the support of a Billy Ray Cyrus cameo, just before Nas came out.

When he won his first 2 Grammys, the gay rapper defied gender stereotypes by wearing in a loud and proud pink cowboy hat, making his sexual identity central to his pop-star identity. Today, Nas has two songs that became the soundtrack of summer (Industry Baby and Montero). Now, he’s saddled up and riding the same trail to normality and acceptance blazed by the Village People in 1978, whose Y.M.C.A. became a sort of queer, gay pride anthem and a mainstream, feel good rally song.

Why It Works

Nas’s bubblegum pink cowboy hat and matching strap leather chest harness and pants cement his sexuality as the centerpiece of his pop star identity. If hetro pop stars can embrace misogyny without criticism, why shouldn’t gay pop stars be able to embrace misandry without everyone getting their knickers in a wad?

How To Wear It

If you know who you are, why hide it? A pink cowboy hat is a friction free way to let the world know you’re out and that you don’t give a hoot what they think about it. Join the Lil Nas X posse, save your breath, and stop living a lie.

The Hat Drops Here 

The Mexicans were the original vaqueros. They taught the Texans how to herd cattle and how to wear cowboy hats long before the Hollywood dream machine homogenized history and repackaged the legend of the cowboy for mass consumption. But whether you’re conservative or liberal, it’s still ok love dress up as a cowboy.

As the celebrated archetype of the American hero, the cowboy hat says America without waving the flag. The cowboy is the enduring symbol of America that crisscrosses over every wedge issue on the political agenda. Whether you’re for or against immigration, birth or gun control, cowboy hats are cool.

The cowboys hats Bezos, Biles, and Nas all wore taking their victory laps prove the cowboy culture is alive and well. But loud and proud isn’t the only way to roll. Alessandro Michel recently introduced Gucci cowboy hats for Spring 2022 in a style more subtle and nuanced. Cowboys are trailblazers and trailblazers set trends and make history, which is exactly what these three in this tale of the cowboy hat trick.

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