WHO: Britney Spears and Justin Timberlake
WHERE: American Music Awards
WHEN:January 8, 2001
Another case of Mouseketeers gone wild, Spears and Timberlake will never live down this matching denim ballgown and suit, even if he now owns a successful--and cool--jeans label. The fact that they consciously chose to coordinate outfits will always mystify us.
Lucy Nicholson, AFP/Getty Images
WHO: Christina Aguilera
WHERE: Blockbuster Awards
WHEN: April 10, 2001
From the shredded velvet gown to the intense darkly-lined lipstick and the curly blond faux fro, there's nothing right about this ensemble.
Aguilera, who has since adopted a more classic style inspired by 1950s pin-up girls, seemed to be going through a typical awkward teenage phase. "Unfortunately, it was for all the world to see," says Thomas.
Kathryn Indiek, WireImage
WHO: Angelina Jolie
WHERE: Academy Awards
WHEN: March 26, 2000
Jolie, who took home a best-supporting actress Oscar for her role in "Girl, Interrupted" that evening, received plenty of attention. Though it was more for her Morticia Adams-like ensemble and making out with her date, er, we mean brother, than she for actually winning the award. While her Wiccan-like look with its long, wig-like black mane and Gothic dress may have been ill-chosen she lightened up later in the decade.
Jamie Thomas, the markets editor at trend-tracking firm Stylesight, feels that since then, Jolie's red carpet style has only improved. "When she became a mother and an ambassador, she really toned down her look," says Thomas.
Ke.Mazur, WireImage
WHO: Kate Hudson
DESIGNER:Stella McCartney for Chloé
WHERE: Academy Awards
WHEN: March 25, 2001
While Hudson's typically a favorite on the red carpet--as are McCartney's dresses--this country singer-inspired violet get-up was "the perfect storm of wrongness," says Berlin.
From a beauty perspective, Hudson's blue eyeshadow and frizzy hair didn't help the situation.
SGranitz, WireImage
WHO: Bjork
DESIGNER: Marjan Pejoski
WHERE: Academy Awards
WHEN: March 25, 2001
Still quite possibly the most insane dress ever to grace a red carpet, you can't help but love Bjork for her choice, even if it is conventionally hideous. What can we say? At least it was entertaining. The swan proved to be great comedic fodder for years to come.
Jeffrey Mayer, WireImage
WHO: Paris Hilton
WHERE: MTV Music Awards
WHEN: August 29, 2002
Celebutante Hilton is continually criticized for her red carpet choices, but this Pepto-Bismol pink two-piece epitomizes everything that's wrong with her style. From the orange-tinged tan to the tie-dyed handkerchief skirt, it can't get much uglier than this.
Evan Agostini, Getty Images
WHO: Lara Flynn Boyle
DESIGNER: David Cardona
WHERE: Golden Globes
WHEN: January 19, 2003
Wearing a costume to a formal event is never a good idea. Boyle's pink tutu was too literal--the (too big) leotard, tulle skirt and toe-shoe heels belonged in a production of Swan Lake, not at an awards ceremony. Save it for Carrie Bradshaw Boyle!
Getty Images
WHO: Drew Barrymore
DESIGNER: Gucci
WHERE: Golden Globes
WHEN: January 16, 2006
Our experts agree: If this beautiful forest green dress had fit well--i.e. if Barrymore had chosen to wear a bra --it would have been an absolute hit.
HFPA
WHO: Fergie
DESIGNER: Etro
WHERE: Teen Choice Awards
WHEN: August 3, 2008
Fergie typically rocks short, fitted dresses on the red carpet. This psychedelic departure from her standard style didn't work out so well. Paired with an over-the-top tan, the singer's red and pink dress and metallic hip belt is difficult to look at. "Musicians can be a bit wilder than actors on the red carpet," says Berlin. "But regardless of the styling, this dress fits horribly."
Jeffrey Mayer, WireImage
WHO: Leighton Meester
DESIGNER: Louis Vuitton
WHERE: Costume Institute Gala at The Metropolitan Museum of Art
WHEN: May 4, 2009
In general we love Meester's penchant for risky red carpet looks, but this is one chance that shouldn't have been taken. Instead of looking high-fashion, the Gossip Girl breakout star resembles a court jester. If only she had skipped the leggings.
Kevin Mazur, WireImage
JBaer, 12-25-2009, 11:11AM
I'm surprised PETA didn't slam Bjork for wearing that swan dress.
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