Saddle Up: The Best Cowboy Hats for Men Who Are Feeling Lucky

Best cowboys hats
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It’s been almost two years since Lil Nas X first released “Old Town Road”, a song that quickly transformed from a novelty one-off to a chart-dominating sensation. But even though the song’s popularity abated, pop culture’s obsession with all things western and Americana in hasn’t. From Diplo and Post Malone’s love of the nudie suit to Instagram accounts that document Americana from a black perspective, pop culture has fixated on the most American myth of them all: the cowboy. Yee-haw!

This renewed interest in Americana has made apparel like men’s western boots popular outside of places like the Deep South and Texas. If you’re interested in this trend but find that denim shirts and Cuban-heel boots are too subtle for you, then you need to invest in a western-style cowboy hat.

Cowboy hats are undoubtedly a bold statement, and they take confidence to pull off. But styled correctly, they won’t make you won’t look like you just stepped off a movie set. An outfit consisting of a white tee and blue jeans is perfectly topped off with a tan cowboy hat. Or finish a suited and booted look with one of the all-black wool hats below. The key is finding the right one that fits your style. We’ve rounded up some of the most stylish (and wearable) cowboy hats, ranging from classics from brands like Stetson to comfortable straw hats for summer. Saddle up, because these are the cowboy hats to buy.


1. Stetson Men’s 6X Open Road Fur Felt Cowboy Hat


No list of cowboy hats is complete without including Stetson, and no list of Stetsons is complete without the Open Road hat. This hat is made from a fur felt and has an oval shape. This hat has a wide flat brim with a rolled edge and dents on the crown, giving it a western edge without feeling too costume-y.

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Justin Men’s 3X Hills Hat


Justin is a trusted boot brand that dates back to the 1800s. In addition to boots, they offer hats that help complete your westernwear look. This hat is made from sheep wool and features a thin, studded band. It features a slight pinch and sharply curved edges for a modern western look.

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Stetson Bozeman Hat


With its slightly shortened brim and leather band, the Bozeman from Stetson sits somewhere between a fedora and cowboy hat. It’s made from wool felt, but the interior sweatband keeps you from getting uncomfortable.

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Pendleton Indiana Hat


The Pendleton Indiana Hat is aptly named; it combines the classiness of a fedora with the adventurousness of a cowboy hat to make a stylish statement that would befit Doctor Jones himself. It has a Scotchguard treatment that helps repel water, and the crushable design makes it easy to throw in your bag without ruining the shape. And since this hat comes from the most legendary American wool mill, you can count on the quality of the fabric.

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Stetson Men’s Skyline Hat


Some of the hats on this list could be mistaken for fedoras or other hat styles, but the Skyline from Stetson is unmistakably a cowboy hat. With its pronounced flared edges, deeply creased dents and pointy metal buckle, this hat is for the most committed cowboy.

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WESTERN EXPRESS Men’s Classic Cowboy Hat


This hat from Western Express has a distinctly western look, featuring an angular brim, pinch crown and leather band. The band also has metal medallions that resemble the buckles on a bolo tie. It’s made from a woven straw material, making it a breathable option.

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