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

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

Not Available Lead
Image via Complex Original
Not Available Lead

losinglead

Not Available Interstitial

feb2007

Not Available Interstitial

aug2008

Not Available Interstitial

nov2008

Not Available Interstitial

When: November 2008

Where: Taking the kids to see Madagascar 2.

Offense: Charlie Sheen's love affair with ugly fedoras and hideous shirts seemingly begins.

feb2009

Not Available Interstitial

When: February 2009

Where: MAGIC tradeshow in Las Vegas, debuting his Da Vinci collection of clothes.

Offense: Bowling shirts (and casual fedoras, for that matter) should never be right up anyone's alley.

mar2009

Not Available Interstitial

When: March 2009

Where: Walking with his baby mama.

Offense: Really dude? Is that all you own in your closet?

june2010

Not Available Interstitial

When: June 2010

Where: Heading to court for sentencing.

Offense: The beanie with a suit... never a good choice. Especially for day when you gotta stand in front of a judge.

aug2010

Not Available Interstitial

When: August 2010

Where: Heading to court... again.

Offense: If the ending theme from Goodfellas was a group of people, they would look like this.

oct2010

Not Available Interstitial

When: October 2010

Where: Leaving a movie set.

Offense: That hat looks like you melted some Skittles on the brim.

oct2010-2

Not Available Interstitial

When: October 2010

Where: Oh you know, just on a froyo break.

Offense: Careful, the heat on your hat might melt your frozen treat.

feb2011

Not Available Interstitial

When: February 2011

Where: Leaving an interview with Piers Morgan.

Offense: Channeling all the wrong parts of Jon Bon Jovi, and wearing a New York City T-shirt in New York is like wearing a band's shirt when watching them play: it makes you look like a total doofus.

april2011

Not Available Interstitial

When: April 2011

Where:  Chillin' at the club.

Offense: Sweatpants and a fedora. Two things that should just never be in the same sentence. Ever.

torpedo

Not Available Interstitial

When: April 2011

Where:  Detroit, kicking off the "Violent Torpedo of Truth Tour"

Offense: We heard he got booed at this show. Our best guess is that it was because of the outfit.

may2011

Not Available Interstitial

When: May 2011

Where:  Hoppin' off the P.J.

Offense: Bootcut sweatpants? They make those? Wow. We just hope they don't have "WINNING" embroidered across the ass.

wendywilliams

Not Available Interstitial

When: September 2011

Where:  Arriving for an interview with Wendy Williams.

Offense: Hole-y crap those are some bad jeans. That shirt is also ballooning way too much up out that tuck. Yeah, we wouldn't want our picture taken in those either dude.

sept2011

Not Available Interstitial

When: September 2011

Where:  At the 2011 Emmy Awards.

Offense: A slight glimmer of hope, dressed to the nines without a hint of untidiness. You should really, really look into a slimmer silhouette though. Who knows? A well-fitting wardrobe could be the beginning of a great comeback.

Latest in Style