Style

#Losing: A Roast of Charlie Sheen's Worst Style Choices

Before you watch his roast tonight, take a look at his laughable style.

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Charlie Sheen's celebrity meltdown seems like a long time ago, but tonight'sComedy Central Roast of Charlie Sheen will likely bring back a flood of memorable memes, Duck Sauce song remixes, and hashtags that have continuously beaten a long-dead horse.

While he's had some great roles in films like Hot Shots and Wall Street, we remember him mostly for his unmistakable style — or complete lack thereof. Whether it was ratty baseball caps, ugly dad jeans, random fedoras, or his penchant for short-sleeve bowling shirts, we took a sieve through memory lane to find the most hilarious "WTF Is He Wearing?!" moments of Charlie Sheen's paparazzi past. Enjoy our gallery of Charlie Sheen's Worst Style Choices.

feb2007

When: February 2007

Where: Omegamania-Antiquorum Preview, Los Angeles.

Offense: Distressed jeans? Tucking in your T-shirt? The 90s ended years ago.

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aug2008

nov2008

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feb2009

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mar2009

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june2010

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aug2010

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oct2010

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oct2010-2

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feb2011

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april2011

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torpedo

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may2011

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wendywilliams

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sept2011

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