Oscar Dresses: All-Time Best (and Worst)

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Bob Riha Jr/WireImage

Penélope Cruz (2007)

The Academy Awards are a place for honoring drama, both onscreen and off — especially in the form of Cruz’s gorgeous Atelier Versace gown with its elaborately feathered train.

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BEST DRESSED

KMazur/WireImage

Michelle Williams (2006)

This mustard-hued, beautifully pleated and tucked Vera Wang swept away any trace of doubt that the former Dawson’s Creek star could make the switch from the small screen to the big time.

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WORST DRESSED

Kevin Winter/Getty

Tilda Swinton (2008)

For any attendee, much less an eventual Best Supporting Actress winner (Michael Clayton), getting ready for the big night should involve more than raiding a box of trash bags from Lanvin.

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BEST DRESSED

Hilary Swank: Kevin Winter/Getty

Hilary Swank (2005)

For her second Oscar win (Million Dollar Baby) the actress chose a unique silhouette in this body-skimming, back-dipping navy Guy Laroche.

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BEST DRESSED

Steve Granitz/WireImage

Renée Zellweger (2001)

With this Jean Desses find from Lily Et Cie, the actress introduced vintage style (and lemony yellow) to the red carpet in a big way.

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BEST DRESSED

Kevin Mazur Archive/WireImage

Nicole Kidman (1996)

It would take quite a dress to upstage Tom Cruise, circa Mission: Impossible. But this chartreuse John Galliano for Dior gown, with intricate embroidering, did just that.

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WORST DRESSED

Steve Granitz/WireImage

Celine Dion (1999)

Is it hard out there for a Best Song nominee? Apparently, as the Canadian singer wore her floppy hat and oversized tux backwards — and badly.

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BEST DRESSED

Russell Einhorn/Liaison

Juliette Binoche (1997)

In a regal gown that broke all the rules — It’s a coat! With a popped collar! In velvet! — the English Patient star (and Best Supporting Actress winner) ruled the red carpet.

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BEST DRESSED

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Julia Roberts (2001)

Her Best Actress winning moment (Erin Brockovich) was completed by the high glamour of this vintage Valentino.

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WORST DRESSED

SGranitz/WireImage

Cameron Diaz (2002)

This awkwardly belted, unfortunately accessorized gown was only made worse by the actress’ fresh out of bed head.

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BEST DRESSED

Kevin Mazur Archive 1/WireImage

Cate Blanchett (1999)

The Best Actress nominee (Elizabeth) netted the fashion accolades in this effortlessly slinky, dramatically embroidered John Galliano gown.

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BEST DRESSED

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Halle Berry (2002)

Carrying on the great tradition of netting (and strategically placed flowers) Berry’s gown proved the star-making power of Oscar’s red carpet — not just for the actress, who garnered a few gasps along with the statuette for her Monster’s Ball turn, but for Elie Saab whose demurely revealing design earned him a spot on the fashion map.

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BEST DRESSED

Jeffrey Mayer/WireImage

Gwyneth Paltrow (1999)

It wasn’t the best fitted gown in terms of its bodice, but the pale pink Ralph Lauren was a perfect fit for the moment when Paltrow tearily accepted her Best Actress statue (for Shakespeare in Love) and ascended to the role of Hollywood’s crown princess.

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WORST DRESSED

Kevin Mazur/WireImage

Gwyneth Paltrow (2002)

The actress didn’t even try to cover up in see-through Alexander McQueen and a bucketful of eyeliner that she must have borrowed from Margot Tenenbaum.

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BEST DRESSED

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Sharon Stone (1996)

When the nominee (Casino) mixed an old Gap tee with an Armani coat and Valentino skirt, the result was high-low chic — and fashion history.

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BEST DRESSED

Kevin Mazur/WireImage

Drew Barrymore (1998)

As the former child star further proved, best dressed doesn’t have to mean designer dresses and cookie-cutter accessories: At this ceremony, an off-the-rack black number and daisies made for an adorable and uniquely Drew look.

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WORST DRESSED

Jim Smeal/WireImage

Demi Moore (1989)

Going casual doesn’t always work, though. Consider this the first commandment of Oscar dressing: No bike shorts on the red carpet. Ever.

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BEST DRESSED

Everett

Grace Kelly (1955)

Her sublime ice blue satin gown has since positioned the Best Actress winner (The Country Girl) as the fashion icon to beat.

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BEST DRESSED

Evan Agostini/Getty Images

Kim Basinger (1998)

And as Basinger proved, if you can’t beat Grace Kelly you could just channel her, which seems to be what the LA Confidential star was doing when she showed up to collect her Best Supporting Actress statuette in pin curls and mint green Escada.

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WORST DRESSED

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Kim Basinger (1990)

Another theory on the actress’s best turn (see previous slide): She was still atoning for this Jekyll and Hyde atrocity.

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BEST DRESSED

Everett

Audrey Hepburn (1954)

You can’t have a conversation about Hollywood icons without mentioning the original gamine, whose classic Givenchy gown made the night of her Roman Holiday win even more noteworthy.

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BEST DRESSED

Kevin Mazur/WireImage

Winona Ryder (2000)

Once the face of slacker chic, turning up in this ’40s-era Pauline Trigere vintage gown took the actress from grunge to glamour.

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WORST DRESSED

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Angelina Jolie (2000)

She should have been happy with her Best Supporting Actress win (for Girl, Interrupted) but in what could only be termed Goth Formal Jolie just looked scary.

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BEST DRESSED

Dan MacMedan/WireImage

Helen Mirren (2007)

In a stunningly bodice-skimming Christian Lacroix, the Best Actress winner (The Queen) gave new life to the term ”silver fox.”

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WORST DRESSED

Jim Smeal/WireImage

Cher (1986)

The actress who elevated worst-dressing to an art form reached her pinnacle in this spider-headdressed Bob Mackie creation.

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BEST DRESSED

Jeff Kravitz/FilmMagic

Uma Thurman (1995)

Can you remember back to a time when no one — not even the devil — wore Prada? It was the Pulp Fiction star’s lavender gown that launched the Italian label into the mainstream.

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WORST DRESSED

Frazer Harrison/Getty Images

Uma Thurman (2004)

It’s a testament to the actress’s beauty that even in remnants from the Sound of Music wardrobe closet she still looked beautiful. But that doesn’t make this puff-sleeved travesty of a Swiss maiden dress from Christian Lacroix okay.

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BEST DRESSED

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Elizabeth Taylor (1970)

Proving the power of the dress, Taylor’s plunging violet gown highlighted her violet eyes — and ensured everyone else’s were on her.

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BEST DRESSED

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Catherine Zeta-Jones (1999)

Picking another perfect hue, this fire-red Versace certified the Zorro star a bonafide siren.

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WORST DRESSED

Jeffrey Mayer/WireImage

Björk (2001)

Eight years after the Icelandic singer first walked the swan down the red carpet, the shock has finally subsided enough that some are starting to defend the avian attire. We’re not buying it. A fluffy white skirt is fine, but next time, please please please…leave the beak at home.

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