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Cowboy hats … straw, felt, leather … men’s, women’s, kid’s … black, pink, white …
the cowboy hat certainly offer a lot more style options than it did back in the day.
Explore the fashion evolution of cowboy hats and see if you can spot where things went wrong.

Robert Duvall's Lonesome Dove Gus Cowboy Hat
The Lonesome Dove "Gus-Style" Stetson Cowboy Hat
Buy a Stetson cowboy hat online and be just like Robert Duvall

Cowboy Hats – The Evolution

Yee haw! Southern style has influenced all Americana, especially when it comes to cowboy hats. Cowboy hats, large or small, have been a popular staple among not only cowboys, but among popular movie stars and performers.

The Handsome, Early Years of Cowboy Hats

Cowboy hats were originally designed to be functional, shielding the eyes and faces of actual cowboys and ranch workers from the ever present hot southern sun. These styles inevitably were copied in popular films depicting western and southern living. John Wayne and Ronald Reagan proudly boasted cowboy hats in their films. These hats were simple, understated, and sans rhinestones or sparkly flare. Ah, memories.

Snoop Dogg's Black Cowboy Hat
Snoop's Doggin' in This Stylish Black Felt Cowboy Hat
"Rap" this black felt cowboy hat around your style now

These cowboy hats also found themselves in the music videos and live performances of country music singers. Garth Brooks and Johnny Cash both wore jet black cowboy hats, giving the trend a new flavor. However, these raven cowboy hats were still simple and stylish. They were still iconic and symbolic of classic Americana. When these fabulous entertainers wore these cowboy hats, they were wearing them as a tribute to all of the great southern stars who had worn them before their time. The look had not yet been corrupted or revamped by Hollywood. However, this would unfortunately all soon change.

Celebrity Mutations: Cowboy Hats Gone Wrong

With such prestige surrounding cowboy hats, it was inevitable that these styles would find their way into music videos and celebrity fashion statements. Snoop Dogg began mutating cowboy hats to fit his own “pimp” style, and the trend quickly infiltrated into popular mainstream culture. Stars like Pamela Anderson and Bret Michaels began wearing strange (and downright ugly) cowboy hats. We began seeing odd hats everywhere – straw cowboy hats, felt cowboy hats, fur cowboy hats. Suddenly, this treasured accessory of Americana went from iconic and classic to sleazy and cheesy.

Rounding up the Celebrity Offenders

Pink Cowboy Hat on Selma Blair
Pink Cowboy Hats ROCK!
Get a Pink Cowboy Hat just like Selma Blair wearsl

To help you understand exactly who these cowboy hats offenders are, we have compiled a list of some of the worst celebs to ever don cowboy hats, in addition to clarifying just why these hats were so heinous.

  • Pamela Anderson's Pink Cowboy Hats
    Pamela Anderson would not last five minutes on a real American ranch. The same holds true for Paris Hilton and Nicole Richie, who attempted to pull of the cowgirl look with flashy felt cowboy hats on their shortly lived television program The Simple Life. Girls, you are not ranch hands. Consider that a blessing because we hear that lounging by the pool and shopping is much easier than farm work.

  • Bret Michaels' Straw Cowboy Hats
    Bret, we understand you. You are struggling to hold on to the very last fifteen minutes of your soon-to-be deceased fame. We don't know if you are trying to endear yourself to middle-aged America by wearing those cheesy straw cowboy hats, but whatever your goal is, it is not working.

  • Snoop Dogg's Fur Cowboy Hats
    Snoop Dogg is not the only rapper guilty of this crime, but he was one of the initial perpetuators. Cowboy hats should be made of sturdy felt or leather and should serve a functional purpose, which is to block out the hot rays of the sun. A fur cowboy hat does nothing besides make your head hot, which is actually counterproductive! Now, we understand that you have a personal assistant who holds an umbrella over you 24/7 to block out the sun, Snoop. Nonetheless, the fur cowboy hats are still cheesy.

If you want to wear a cowboy hat as a subtle tribute to classic Americana, perfect! However, avoid anything pink, shiny, or furry. The message that these cowboy hats sends is: "I'm not really a cowboy, but don't tell anyone. Despite the fact that I have millions of dollars in the bank, I would prefer to be considered just an average Joe. You know, one who... sweeps their guest house themselves...or drinks their five hundred dollar bottle of cheap champagne from just an ordinary mug. Wait, what do regular people do again?

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