17 athletes trying to pull off a fedora

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One of the perks of being a professional athlete is that you’re automatically pretty cool. In fact, athletes are so cool, they can make unpopular things seem awesome by association – just look at Russell Westbrook’s line of hipster glasses or JaVale McGee’s weird Segway obsession. But there are some things so truly uncool that they make even professional athletes seem like real nerds.

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Case in point: the fedora. What was once a fashion staple of such classy men as Sinatra and Bogart is now the internet’s punching bag. Made stunningly unpopular by high school freshman who paired the hat with faded Staind tee shirts and Lee Dungarees, the fedora’s reputation has experienced a spectacular fall from grace.

But this hasn’t stopped athletes from at least trying to wear the ubiquitous hat. Here, we’ve assembled a collection of some of the coolest men and women on Earth attempting to pull off one of the least-cool accessories possible, with varying success. (And yes, hat nerds, there are some Trilbies in here, too. Deal with it.)

1. Arian Foster

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Let’s start with some good news: Arian Foster is making a great argument on behalf of the fedora. That color-coordination with the tie, the scarf, and the hat? A+. That being said – would the outfit be even better without the hat?

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2. Brett ​Keisel

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Can... can he see?

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3. Ben Roethlisberger

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In this hat, Ben Roethlisberger looks like a movie bad-guy’s dopey sidekick. This picture might be a scene from a movie where he accidentally wandered into a press conference in the middle of a heist, and just had to go with it.

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4. Usain Bolt

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“Mom take a picture of me for MySpace.”

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5. Barry Zito

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It almost feels wrong to include Barry Zito on this list, because his hat is such a press conference staple that I think it actually might be part of his head. We’ve included it for nostalgia’s sake, since he won’t be appearing in any Giants press conference during the World Series, and because it’s the only hat on this list to inspire its own Twitter account.

Hip to be square: The nerdiest athletes in sports

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6. Tim Tebow

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“Bro this year’s Spring Break is going to be Legen – wait for it – dary.”

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7. Antonio Brown

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Another strong case on behalf of the fedora. I guess if we’ve learned anything, it’s that you have to plan your whole outfit around that one statement accessory. And also, for some reason fedoras work better with a bow tie. I guess two wrongs do make a right?

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8. Dwyane Wade

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There is so much wrong with both of these outfits.

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9. Maria Sharapova

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This is actually a picture for Kate Winslet’s charity, the Golden Hat Foundation, so I won’t mock the fedora in this picture. However, I guarantee if you scroll through Maria Sharapova’s phone, there will be 67 other attempts to take this selfie before she landed on the one she actually used.

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10. LeBron James

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This is the face of a man who has just realized what his outfit looks like.

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11. Royals fans

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Who would win the World Series if it weren't based on baseball?

Congratulations to the Royals on making it to the World Series and playing the greatest prank of all time on your fans by making them wear these hats! The fedoras were part of a tribute to the Monarchs, one of the most storied Negro League teams in baseball. The #DressedToTheNines promotion was commendable in theory, but when a fancy hat is accompanied by a cheese-stained Royals tee, is that really 'dressing to the nines'? 

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12. Shaun White

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I mean, I guess if you’re going to pretend to be a rock star, you could do a lot worse than pretending to be Jack White. Wait… Shaun White… Jack White… CONSPIRACY.

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13. Carmelo Anthony

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This look is not being helped by that pencil-thin mustache.

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14. Ryan Lochte

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“Greetings, m’lady. What’s your name?”

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15. Shaq

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Strictly from a comfort perspective – a velvet fedora has to be hot, right? There’s no way that fedora isn’t covered in Shaq-sweat.

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16. Caroline Wozniacki

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“After a tough week working in PR, I love getting tipsy with my girlfriends at Cheesecake Factory brunch.”

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17. Justin Timberlake

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OK, he’s not a professional athlete, but he is playing golf in this photo, and frankly, it’s always a good idea to end an article of any kind with a photo of JT, even if he’s wearing a fedora.

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