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Fashion Disasters: 14 Worst Dressed Celebrities

Since the dawn of celebrity, fame and fashion have gone hand-in-hand. Musicians, actors, and artists of all kinds dream of walking down the red carpet to the flash of paparazzi cameras and adulation from their peers – all the while looking as glamorous as possible. And from the Academy Awards, to the Grammys, to the millions of openings, parties, and events happening year-round in Hollywood, everyone aims to look their best. However, sometimes there are these famous individuals that either never quite figure out how to dress, or end up trying too hard and failing miserably. The following 14 examples of how badly celebrities have messed their images up.

CHER

In the mid-1980s, there were very few pop stars bigger than Cher. Having successfully resuscitated her singing career, Cher cut her acting teeth with critically acclaimed roles in Moonstruck, and The Mask among others. She ultimately won an Academy Award for her role in the former. But, at the 1986 Academy Awards, Cher showed up in this number looking more like an evil peacock with an unusually large face, than an award-winning actress.

MADONNA

Iconic. Revolutionary. Ground breaking. All these adjectives describe Madonna’s musical career. From the 1980s through to today, Madonna has sold tens of millions of records and constantly adapted to the times both her music and look. In 2008, Madonna was inducted into the Rock and Roll Hall of Fame, however on the night of her induction she looked more ready to attend the funeral of Abigail Williams than to accept the historic honor. She also has manly arms.

ROSE McGOWAN

Dating a shock rocker notorious for his outrageous dress and antics can have both its positives and negatives. You gain an instant VIP pass to all the coolest parties and events and may find yourself in paparazzi rags on a regular basis. But ,you also may be find yourself upstaged just as frequently. On the night of the 1998 MTV Video Music Awards, Rose McGowan showed up in a see-through gown that had less composition than the latest Michael Bay film script. While her look seemed good to adoring seventeen year-old boys everywhere, it ultimately proved bad for her career.

BJORK

From the “What were they thinking?!” pile comes this gem of a photo. Bjork, the tremendously eclectic Icelandic songstress took time out of her busy schedule to film a movie with Lars Von Trier, the widely acclaimed film Dancer in the Dark. Equally not as acclaimed was her portrayal of a swan, pictured above.

COURTNEY LOVE

The grunge rock movement spawned many still famous figures: Eddie Vedder, Chris Cornell, and of course, the late Kurt Cobain. But perhaps none was more controversial that Courtney Love. During the late 1990s, Love turned her attention to acting, starring in Man On the Moon, and The People Versus Larry Flynt. The result of the mixture of glam and grunge – garbage bag dress. Grunge chic perhaps? Perhaps not.

MICKEY ROURKE

A leading man in his heyday, Mickey Rourke surgically altered his face in the early 1990s for unknown reasons (was he drunk?). After disappearing from the silver screen for nearly two decades, Rourke was out of the red carpet world until recent supporting roles in Domino and Sin City. It was not until 2008 that Rourke made his Hollywood comeback complete, with the release of, and subsequent Best Actor nomination for The Wrestler. Known for his bad boy image Rourke is trying to re-brand himself as a young, hip, Hollywood A-lister. But he turned out resembling a r’oided-out pirate, in touch with his feminine side.

BRITNEY SPEARS

The stresses of celebrity can weigh heavily. After conquering the pop charts and selling millions of albums, Britney Spears’ world came crashing down. Prior to her complete meltdown, photos surfaced of her drunk and on drugs, underwear-less and ultimately looking like a trainwreck. She eventually lost custody of her children and was heavily scrutinized by the general public. From the height of her demise comes this intoxicating monstrosity .

MARILYN MANSON

When shocking people is part of your daily regimen, you’re probably not shopping at The Gap. And, unnecessarily long sleeves, crazy eye make up and militia boots are all part of the norm for the dress of this modern day musical vampire. But, Marilyn Manson never ceases to look like a combination between an alien and a albino child with ill-fitting garments.

RAVEN SYMONE

Oh, the 1970s: a decade of promiscuous sex, cocaine, disco, and bad haircuts. Unfortunately for Raven Symone, this picture was taken roughly 30 years after this era ended. The large-nostriled teen icon (above) seems to loved Ed Hardy so much, she made a shirt/dress out of one of his windbreakers. I don’t know why anyone even took a picture of her….But lucky for you, we cropped her face out of the picture.

THE PUSSYCAT DOLLS

The Pussycat Dolls are known for their on-stage sexual antics, and for being very attractive. Even though their fans consist almost exclusively of adolescent girls, TPD tend to dress as if they belong in a Spearmint Rhino. While you couldn’t take any of them anywhere, this picture has me wishing I was at a Spearmint Rhino, rather than writing this.

RUSSELL BRAND

Making a splash this year in the box office hit Forgetting Sarah Marshall, Russell Brand was became an unexpected favorite character of many movie-goers. Gaining roles in the upcoming Get Him To the Greek, and making controversial waves with his BBC radio show, Brand is currently at the height of his celebrity thus far. Suffice to say, he is one of the funniest Brits around, but his style seems to be derived from old Cure videos and maybe even a Robert Smith estate show or two. And, his hair reminds me of a diner I once stopped in at while on a cross-country road trip, where all the waitresses had the same teased 80′s big hairdo.

ASHTON KUTCHER

Ashton Kutcher has had quite a ride during the last decade with roles in a slew of semi-successful to relatively successful TV shows and movies. And he really seems to do it all: model, actor, producer, douche. But most recently, he is beginning to make a name for himself by fully embracing the ‘Brokeback Moustache’ look. It seems as if this is the result of his fashion/style consultant getting back at Kutcher for him embarrassing at a restaurant or something asinine.

ARETHA FRANKLIN

F-U-G-L-Y. Find out what it means to me…

JOSS STONE

A sultry, soulful voice – transcontinental appeal – absolute beauty. Joss Stone has all the tools of a great pop songstress, except that she perenially looks as if she dressed herself in the dark. Considered by some a sonic throwback to the days of great R&B, Joss Stone is proves that sometimes reaching for an older sound can lead to something fresh and innovative. Someone should have told her not to wrench her arm that far back when it comes to dressing herself, however. Because, this clown vomit-themed number just is utter garbage.