Style

The Biggest Celebrity Style Fails and Wins of the Week

'Tis the season to be swaggy, or nah-nah-nah-nah-nah-nah-nah-nah-nah.

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Even though celebrities are flush with influence and cash, there are only a few that consistently kill it when it comes to style. That's why when they do it consistently, we give them credit in our Best Dressed of the Year rankings. The rest of the time, they're just like us when it comes to hits and misses. But since they're constantly in the spotlight, the hits and misses are magnified instantly. Each week, we honor those who rise to the challenge of dressing well, and shade those who clearly threw up a brick. These are The Biggest Celebrity Style Fails and Wins of the Week.

Win: Evan Ross

Where: Los Angeles

You got the (Jamba) Juice now, Evan Ross! Topcoat game so strong dude needed two protein shakes to be able to sustain that level of stunt.

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Fail: Seth Green

Where: New York

Things we hope Seth copped at Barneys: new jacket, new hat, new shades, new shirt.

Win: Rihanna

Where: New York

Rihanna is no stranger to menswear, and seeing this look on a dude would be equally swaggy—but no person on this planet could make this look cooler than RiRi.

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Fail: Corey Gamble

Where: Los Angeles

Kris Jenner's new boo is really trying with the side vent hoodie, but the baggy pants and swagless sneakers ruin the whole look. Get some slim sweats, fam... and we all know you can afford Jordans.

Win: Kanye West

Where: New York

Yeezy and RiRi were spotted leaving the same studio in matching boots. Rumor has it they were recording a new song called "A-L-P-H-E-T." We made that up, but that would be fye though, right?

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Fail: Bruce Jenner

Where: Thousand Oaks, CA

Bruce Jenner picked up some shifts at Target so he could have a little extra cash for Christmas gifts—stars, they're just like us! Sadly, the #brucefromtarget meme totally bricked before it could become a thing.

Win: Jay Z

Where: New York

Jay Z channels a more tailored version of '90s hip-hop style in straight-cut denim, wheat Timbs, and a cozy shearling jacket that probably costs more than Blue Ivy's projected college tuition.

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Fail: Robert Downey Jr.

Where: Los Angeles

Robert Downey Jr. is dressed like the token stoner in every other college dormitory.

Win: Shia LaBeouf

Where: Los Angeles

This is how you feel when you finally convince a girl to come over so you can cook dinner for her and you spend like $200 on food because you know you're probably gonna smash but don't want to get overexcited.

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Fail: P. Diddy

Where: St. Barts

But like, doesn't P. Diddy have an intern for this shit? Or maybe one of the people from Making the Band chained to the bow of the ship ready to get cheesecake or Cambodian breast milk at a moment's notice?

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