From the first private banquet ceremony held in 1929 to the star-studded, massive see-and-be-seen affair that it is today, the Academy Awards has served as Hollywood’s — and fashion’s — biggest night out. In addition to questions about who will win what, everyone also wants to know who will wear what. And Tinseltown never disappoints. Here, feast your eyes on the 13 best dresses ever worn to the illustrious awards ceremony.
1. Audrey Hepburn, 1954
When Audrey Hepburn stepped on to the stage to accept her Oscar for Roman Holiday, she made history — and not just for her win. Her white floral Givenchy dress, which perfectly exemplified her unique blend of girlishness and sophisticated elegance, charmed the crowd and stands out as one of the most iconic Oscar dresses of all time.
2. Michelle Williams, 2006
Photographers and fellow actors alike got whiplash at the 2006 Academy Awards thanks to Michelle Williams’ bold, exquisite saffron-colored Vera Wang gown. The 1930s-inspired cut and pleats perfectly accentuated the blonde beauty’s willowy frame and the color was nothing short of striking. It has become an unforgettable Oscars look.
3. Cameron Diaz, 2010
In her strapless, champagne-colored, gold-paillette-encrusted Oscar de la Renta gown, Cameron Diaz looked positively stunning — classic, radiant, and timelessly elegant.
4. Heidi Klum, 2008
Sizzling as always, model and Project Runway host Heidi Klum stormed the red carpet at the 2008 Oscars in a striking, fitted, red Galliano dress. The silk taffeta gown had a show-stopping high collar and sweeping train.
5. Kate Winslet, 2002
Speaking of red, Kate Winslet donned an exquisite Ben de Lisi gown with an intricate, delicate floral accent across one shoulder in 2002. She looked bold yet perfectly poised.
6. Emma Stone, 2012
And finally, still on the red train, only Emma Stone could make it look this sweet: Her Giambattista Valli couture gown in 2007 — which was more “raspberry” and less “fire engine” — had a flowing simplicity that suited her well, and the billowy bow at the neck was the perfect accent.
8. Maggie Gyllenhaal, 2010
It was a bold choice, but one that definitely worked: Maggie Gyllenhaal’s column-shaped Dries van Noten dress looked almost like a watercolor painting, featuring a bright blue background with the occasional dark green leaf, tapering off to white at the ankles. It was quirky, fresh, pretty and daring — just like the actress herself.
9. Penelope Cruz, 2002
Embracing her Spanish heritage (and highlighting her gorgeous curves), Penelope Cruz wowed in a black lace Ralph Lauren frock with drop-shoulder sleeves and an open back.
10. Hilary Swank, 2011
Hilary Swank looked ladylike in a Gucci Premiere couture strapless gown that tapered off into what looked like an ostrich-feather train, which deepened in color from silver gray to a rich navy blue. Fun yet fancy.
11. Anne Hathaway, 2011
We were used to seeing her sweet and innocent, but Anne Hathaway shook up her good-girl image with this daring, maroon silk Versace gown. The vintage design on the tight bodice was modernized with flowing pieces of chiffon at the hip.
12. Hally Berry, 2011
Hally Berry’s nude, crystal-encrusted, mermaid Marchese gown, with an ethereal organza and silk tulle train, accented the actress’ caramel skin and showed off her amazing figure (she was 44 years old at the time!).
13. Angelina Jolie, 2009
OK, so it wasn’t the dress that wowed (just a simple, black, strapless Elie Saab number), but Angelina Jolie’s accessory deserves a shout-out: The exquisite, emerald-green teardrop Lorraine Schwartz earrings cost a jaw-dropping $2.5 million, and were bona fide bedazzlers.