The 20 most unforgettable Oscar dresses

The 20 most unforgettable Oscar dresses
Gwyneth Paltrow
Gwyneth took a lot of flack from the tabloids for this braless 2002 Alexander McQueen look, and later admitted to Vogue it wasn’t her favorite. “There were a few issues,” she said. “I still love the dress itself, but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to — a little bit of punk at the Oscars.”
Angelina Jolie
Angelina Jolie made a serious goth statement in 2000, picking up her first Academy Award in a long-sleeved black Versace gown with long black hair extensions.
Kate Hudson
Kate Hudson celebrated her first nomination with a custom Stella McCartney dress that, paired with a unique updo, landed her in fashion hot water. “I turned on the television to find out I was on every ‘Worst Dressed’ list possible,” the actor told Vogue. “So I called Stella and we just laughed our arses off and she said to me, ‘Look babe, it was the hair wasn’t it?'”
Celine Dion
Over the past few years, with the help of superstar stylist Law Roach, Celine has become a fashion force to be reckoned with. But way back in 1999 she showed she already had a penchant for taking risks with a white backwards suit and hat by John Galliano for Christian Dior.
Björk
Created by designer Marjan Pejoski, the infamous dress was designed like a swan, and at the ceremony in 2001, Björk mimicked laying an egg on the red carpet.
Cher
A reminder of why we miss seeing Cher on red carpets. This bejeweled look from Bob Mackie ruled the red carpet that year, and it lives in our hearts forever.
Faith Hill
Attending the awards show to sing “Somewhere Over the Rainbow,” Faith Hill gave a unique nod to the legendary Wizard of Oz tune with her pastel Versace design. “Since she was wearing black onstage, we wanted to do something colorful for the carpet,” her stylist Garth Condit told People at the time.
Gwyneth Paltrow
The dress that divided the nation in 1999. Was Gwyneth’s pink Ralph Lauren dress a sweet, appropriate dress for a young actress picking up her first Oscar, or an ill-fitting, wrinkled prom queen nightmare? The debate rages on.
Hilary Swank
The multiple Oscar winner selected an illusion dress from Christian Dior in 2005 that highlighted her toned arms and legs, but many felt the look was too casual for the event.
Jennifer Hudson
Hudson picked up her 2007 Best Supporting Actress statuette in a simple (and sort of frumpy) brown taffeta gown, which she topped with a polarizing metallic python jacket.
Juliette Binoche
Binoche went with a mixed look at the 2001 awards, pairing a flapper look above the knees with leather boots on the bottom.
Mischa Barton
Oscar gold is a common choice for the Academy Awards after-parties, and Barton hopped right on that trend.
Madonna
Madonna has remained a style chameleon for decades, and she gave us major disco vibes in this 2006 Versace number. The feathered hair makes the look.
Nicky Hilton
Cutouts are back, but a brunette Nicki Hilton wore it at Elton John’s Oscar party way back in 2005.
Sally Kirkland
Sally Kirkland is an annual Academy Awards treasure with her over-the-top looks. This flouncy 2002 gown is one of her most unique.
Selma Blair
You have to applaud Blair’s risky 2002 dress. But the visible panties through the fringe might have been a bit much.
Sarah Jessica Parker
This Chanel couture gown was a risk for Parker, as it didn’t move well on camera, and her neck looks a bit choked. That said, who can pass up Chanel?
Cameron Diaz
Cameron belted her floral-print 2002 Ungaro gown and added antique Indian jewelry to create a red carpet look that suited her boho vibe.
Tilda Swinton
The always androgynous Swinton gave major artsy vibes in this black velvet Lanvin in 2008.
Uma Thurman
Uma Thurman can wear anything she wants, and at the 2004 Academy Awards, she did.
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