The 10 Best and Worst Oscar Dresses Ever

With the 82nd annual Academy Awards coming up, we've rounded up some of the most buzzed-about hits and misses in red carpet history. Let's see if the starlets who walk the carpet this year will keep these looks in mind in terms of what to aim for - and what to steer wayyy clear of. Let's none of these actresses give their stylist the day off this year.

Worst Dressed: Demi Moore in her own design, 1989

Someone should either find the other half of her skirt or point her in the direction of the nearest cycling club. Thankfully, Demi left her subsequent wardrobe choices to the pros.

Best Dressed: Angelina Jolie, 2004

Angie's one of very few people who can rock this material and this color - both being mercilessly unforgiving. But the dress drapes on her curves and shows off her assets in all the right ways. No surprise, she also had one of the best hairstyles at last year's Oscars.

Worst Dressed: Bjork, 2001

Between the nude-colored bodysuit, the bejeweled tights, and umm...the fake swan wrapped around her neck, we're not sure if Bjork should be swimming in the lake or skating on the ice.

Best Dressed: Michelle Williams, 2006

Coupled with the bright red lips and wispy hair, Michelle's saffron Vera Wang dress makes her look like she's straight out of an old Hollywood film. The cut makes her body look amazing, especially considering that she had given birth to Matilda just three months before. Find out how to get the best Oscar make-up looks.

Worst Dressed: Gwyneth Paltrow, 2002

The see-through vest made Gwyneth's breasts look flat, the shapeless skirt made her waist disappear, and the ruched material just made everything look sloppily bunched up. She insisted that she loved the dress, but we know better.

Best Dressed: Halle Berry, 2002

Probably one of the best-known Oscar dresses of all time, it shows off Halle's best parts, while the strategic embroidering still leaves something to the imagination. There's a lot of material on the bottom half, but it doesn't swallow her up or hide the shape of her legs.

Worst Dressed: Hilary Swank, 2003

It looks like Hilary thought her pale pink mini dress wasn't up to the occasion, so she looked around until - aha! - she found a piece of hot pink gauze to wrap around herself. The Jimmy Choos are pretty sexy, though.

Best Dressed: Penélope Cruz, 2007

Penélope ruffled a lot of feathers - pun intended - with this dress. People either loved it or hated it big-time. We're signing up for the first group. It's a gorgeous color, fit her perfectly, and was a bold choice that she gets major points for pulling off. She was one of Hollywood's most fashionable ladies on the red carpet again this year.

Worst Dressed: Charlize Theron, 2006

There's just way too much going on here. It seems as though a handful of fabric strips were randomly tacked onto the bodice of the dress at the last minute for no logical reason. And the cherry on top? That gigantic and ill-placed bow on her left shoulder. Yikes.

Best Dressed: Keira Knightley, 2006

Keira looks super-graceful in this eggplant taffeta gown custom-made by Vera Wang. The multicolored Bulgari necklace adds even more elegance to an already sophisticated look. Keira donated this dress to Oxfam International for an auction, and it raised $7,900, which went toward the food crisis in East Africa.

Plus: Find out how you can decide what the Oscar escorts wear to this year's event.

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Reprinted with permission of Hearst Communications, Inc.