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Best and Worst Oscars Fashion Ever

The Oscars is like a grand, celeb-studded fashion show -- stars dress to impress, and there's no reward for playing it safe. In this rundown of the 40 best and worst looks in Academy Awards history, we honor those who took a chance and dazzled on the red carpet ... and call out those who went out on a limb and flopped. See which big name risk-takers made our list. -- By Maggie Furlong

Best and Worst Oscars Fashion Ever

Worst: Work It Out

Demi Moore attempted to make eveningwear more athletic at the 1989 awards, designing her own ensemble that paired a long, open-front, gold embroidered skirt with a bustier and biker shorts -- yes, biker shorts. Needless to say, we're glad she stuck to acting.

Best and Worst Oscars Fashion Ever

Best: Pretty Woman

With three Academy Award nominations under her belt, Julia Roberts took home her first Oscar in 2001 for 'Erin Brockovich' wearing a dress as special as the occasion: Her black column gown with tulle skirt and white piping detail was vintage Valentino Couture.

Best and Worst Oscars Fashion Ever

Worst: This Isn't the SAGs!

No one will ever call Gwyneth Paltrow best supported actress after her undergarment-challenged showing at the 2002 Oscars. Her makeup, hair and jewelry were all wrong for the occasion, but it was the Alexander McQueen sheer mesh top and black skirt that caused jaws to drop lower than her chest had.

Best and Worst Oscars Fashion Ever

Best: Making History

As if being the first African American woman to win a Best Actress Oscar wasn't enough, 'Monster's Ball' star Halle Berry stole the show with her style as well in 2002, in a daring Elie Saab creation with a deep red ball skirt wrapped around the sheer embroidered top.

Best and Worst Oscars Fashion Ever

Worst: Remember When?

Before Nicole Kidman became a red carpet icon, she fell victim to the awkward trends of the early '90s along with then hubby Tom Cruise. Their 1991 Oscar appearance was memorable only in its ridiculousness, with Nic in a short black velvet number with a bizarre sequin belt attachment, and Tom in an oversized tux.

Best and Worst Oscars Fashion Ever

Best: At a Store Near You

Sharon Stone made headlines -- and everyone's best dressed list -- in 1999 when she paired her lavender Vera Wang ball skirt with a white Gap button-down that she snagged from her husband's closet. A $29.99 wardrobe basic has never looked this beautiful.

Best and Worst Oscars Fashion Ever

Worst: Back in Black

Before Angelina Jolie became a do-gooder mother of the world, she preferred to show her darker side. Blood vials, plenty of leather and, in 2000, jet-black hair and this goth Versace gown. She was clearly feeling bold: This was also the night of her infamous smooch with big bro James Haven.

Best and Worst Oscars Fashion Ever

Best: The Heat Is On

Wearing red on the red carpet isn't easy, but in 1999, 'Zorro' beauty Catherine Zeta-Jones set the Oscar's arrivals walkway ablaze, looking effortlessly sexy and pulled together in this ruby strapless Versace gown with sparkly threading detail.

Best and Worst Oscars Fashion Ever

Worst: More Than Half Bad

To sleeve or not to sleeve -- that was the question for Kim Basinger at the 1990 Oscars. Her poufy princess dress was half gown with a glove and half collared, long-sleeved jacket on top. She had no one to blame but herself: She designed this all on her own.

Best and Worst Oscars Fashion Ever