1999
Celine Dion
The singer was obviously told it was backwards day. It’s impossible that she could actually think a John Galliano tux worn in reverse looked fashionable.
Gwyneth Paltrow
Most people borrow jewels during award season. But the Best Actress winner’s $160,000 40-carat Harry Winston necklace that she wore with that iconic pink Ralph Lauren gown was a gifit from her parents.
2000
Tyra Banks
The supermodel looked like a prom queen in a lavender Vera Wang ballgown. But the Academy Awards is not exactly high school.
Angelina Jolie
The gothic Versace dress and pink straight hair were tame in comparison to Angie’s onstage antics. That was the year she kissed her brother when she won Best Supporting Actress for Girl Interrupted.
2001
Julia Roberts
The Best Actress winner for Erin Brockovich made everyone swoon in vintage Valentino. Not only was it one of—if not the—best fashion moment for Julia, it was one of the prettiest Oscar looks of all time.
Björk
Thanks to the Marjan Pejoski feathered costume, it’s impossible not to think of the Icelandic singer when you see a swan. It’s equally as hard to forget this Oscar disaster every time you hear Björk’s name.
2002
Halle Berry
The Best Actress winner’s Elie Saab gown was just as memorable as her sobbing acceptance speech. And both were absolutely stunning.
Kate Winslet
Designer Ben de Lisi custom designed the actress’s one-shoulder dress, and his hard work paid off. She was red-hot on the red carpet, landing on almost every best-dressed list.
2003
Hilary Swank
Princess pink worked for Gwyneth Paltrow in 1999, but not so much for Hilary four years later. While the design is surprisingly very on-trend (exposed lingerie is all the rage), the actress is better suited for the sophisticated style she learned to wear later on.
Kate Hudson
The actress showed off her golden girl status in a Versace gown and sunny glow.
2004
Jennifer Garner
The actress shined like a sun goddess in a vintage orange Valentino gown and gold Fendi clutch.
Uma Thurman
If it was Halloween, she would have made a magnificent Swiss miss. But when she stepped onto the Oscars red carpet in Christian Lacroix, everyone dropped their jaws—and not in a good way.
2005
Natalie Portman
The petite brunette took command as a fashion goddess in a metallic Lanvin gown and sparkly headband.
Charlize Theron
It’s no wonder the actress is so loyal to Dior. Designer John Galliano designs gowns, like this powder-blue tiered masterpiece, that look as if they were specifically made for Charlize.
2006
Reese Witherspoon
Reese sparkled like royalty at the Oscars and it’s no wonder why: The Dior dress she found in a vintage shop in Paris once belonged to a princess!
Michelle Williams
The marigold Vera Wang, soft side updo and dramatic red lip was probably the actress’s all-time best red carpet moment. It was such a stunning statement that four years later Diane Kruger channeled Michelle at the SAG Awards.
2007
Penélope Cruz
The Best Actress nominee didn’t win an Academy Award, but she sure won everyone’s fashion praises in a dramatic Atelier Versace blush gown.
Kirsten Dunst
The actress proved that just because something is haute couture does not mean it’s hot or chic. Her Chanel dress had too much going on between the feathers, embroidery and Peter Pan neckline.
2008
Diablo Cody
If you’re going to do leopard, a thigh-high slit is certainly not necessary. And flats on the red carpet?! What was she thinking? The Juno writer may have picked up an award for Best Original Screenplay, but she needed to go back to the fashion drawing board.
Marion Cotillard
The French beauty was a marvelous modern mermaid in Jean Paul Gaultier, warming our hearts even more with her joyous acceptance speech for Best Actress in La Vie en Rose.
2009
Miley Cyrus
The teenage star said her Zuhair Murad haute couture dress weighed more than her, but it sure was gorgeous!
Anne Hathaway
The actress looked like a decadent glass of bubbly in an Armani Privé mermaid gown and more than one million dollars worth of Cartier diamonds.
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ONTD what has been your favourite Oscar dress and who are you most looking forward to seeing this year?
