The Best Oscar Gowns—Ever!

We can’t say the word Oscars without automatically thinking of the striking black-and-white Valentino that Julia Roberts wore to accept her best-actress award for her role in Erin Brockovich. Her high-glamour look reminds us that sometimes simplicity is best.

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You might not be familiar with old-Hollywood guru Edith Head—who, with her eight Oscar wins for costume design, garnered more Academy Awards than any woman in history—but you’ve definitely seen her work. Think Rear Window, Sabrina and To Catch a Thief—oh, and this ice-blue princess-y dress that Grace Kelly wore to receive her best-actress award for Country Girl. The simple gown cost $4,000 to design, reportedly making it the most expensive dress in Oscar history—up to 1955, that is.

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Shunning the pressure of trying to find the perfect dress, Sharon Stone shook up the 1996 Academy Awards by showing up in an old black tee from the Gap, styled up with a Valentino skirt and a velvet Armani coat. How genius is that?

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By the time Halle Berry made Academy Award history in 2002 as the first African-American woman to win the best-actress award, she’d already won everyone’s hearts on the red carpet hours earlier. Turning up in a claret-color Elie Saab gown—complete with strategically placed floral appliqués—Berry announced to the viewing world that she was about to steal the show.

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The scallop details on the ivory gown Marion Cotillard wore to accept her best-actress award in 2008 left fashion lovers in two camps: those who swooned and those who wrinkled their noses. We happen to love the sweet look, especially the way it accentuates a woman’s body with a little wink. And besides, any woman who can successfully pull off the mermaid thing certainly deserves the title of best dressed.

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Every woman well versed in fashion DOs knows that if you want to get noticed, wear red. The style rule must have been on Catherine Zeta-Jones’ mind when she chose this strapless red Versace dress for her first-ever Oscar appearance. The result? A Hollywood star was born.

Here’s proof that you can avoid the dreaded “fussy” judgment while sporting more pleats than a JV cheering squad. Marisa Tomei arrived at the Academy Awards in a formfitting one-shouldered origami-inspired gown with a small train and still managed to look elegant and effortless.

Though Audrey is best known for the LBD and the princess gown she wore the night she won her Oscar for Roman Holiday in 1954, the woman always had style. Case in point: the super-ladylike black-and-white dots-and-stripes ensemble that Hepburn wore to the Academy Awards in 1988. The creation echoes her iconic black-and-white look in My Fair Lady and proves you can stun a crowd at any age—especially if you’re Audrey Hepburn, right?

In one of the most memorable Oscar fashion moments ever, Cate Blanchett slipped into a tight purple John Galliano dress, showcasing her back beneath a sheer overlay embroidered with butterflies and a hummingbird. The sweet look immediately drew public adoration, and Cate loved it too, reportedly calling the dress her “fashion orgasm.”

Leave it to Drew to play up a simple slinky black dress with a live flower and a face-framing bleach-blond hairstyle. Not only does she look as adorable as ever, but the dark lips, thin brows and blunt bangs scream ’90s perfectly—we’re sure the look inspired more than one bold lip before the turn of the aughts.