Cher, 1986(01 of61)
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Hilary Swank, 2003(02 of61)
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Lizzy Gardiner, 1995(03 of61)
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Uma Thurman, 2004(04 of61)
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Demi Moore, 1989(05 of61)
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Kim Basinger, 1990(06 of61)
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Kate Winslet, 1996(07 of61)
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Celine Dion, 1999(08 of61)
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Kate Hudson, 2001(09 of61)
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Bjork, 2001(10 of61)
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Anjelica Huston, 1975(11 of61)
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Farrah Fawcett, 1978(12 of61)
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Goldie Hawn, 1978(13 of61)
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Donna Summer, 1979(14 of61)
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Meryl Streep, 1980(15 of61)
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Sally Field, 1980(16 of61)
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Nicole Kidman, 1997(17 of61)
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Gwyneth Paltrow, 1999(18 of61)
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Angelina Jolie, 2000(19 of61)
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Bjork, 2001(20 of61)
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Olivia De Havilland (left), 1950(21 of61)
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Audrey Hepburn, 1954(22 of61)
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Grace Kelly, 1955(23 of61)
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Ava Gardner, 1960(24 of61)
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Barbra Streisand, 1968(25 of61)
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Barbra Streisand, 1969(26 of61)
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Raquel Welch, 1970(27 of61)
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Jane Fonda, 1970(28 of61)
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Cher, 1973(29 of61)
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Elizabeth Taylor, 1976(30 of61)
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Diane Keaton, 1976(31 of61)
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Demi Moore, 1989(32 of61)
Open Image ModalWe’re glad Demi stuck to her day job: in 1989, she designed her own look for the red carpet and the result was not pretty. From the heavy velvet train, to the gold push-up bra, this has to be one of the worst Oscar looks ever. \n\nWe understand it was the ‘80s, but as a hard rule, bicycle shorts never belong on a red carpet. (credit:Getty images)
Audrey Hepburn, 1953(33 of61)
Open Image ModalBesides the LBD in Breakfast at Tiffany’s, this Hubert de Givenchy gown became one of Audrey’s most famous looks, and for good reason – the delicate flowers and darling silhouette accented her feminine, elfin features beautifully. \n\nShe accepted her award for Best Actress for her role in Roman Holiday with trademark grace and poise, and the ‘Audrey look’ we know today was born. (credit:PA Photos)
Cher, 1986(34 of61)
Open Image ModalCher’s never been one to shy away from outrageous red carpet looks and in 1986, she upstaged even herself by showing up to the Oscars in this infamous, midriff-baring creation by Bob Mackie. The Las Vegas Showgirls headpiece kind of made her look like a sea urchin -- albeit, a sea urchin with a rockin’ bod. (credit:Eugene Adebari/Rex USA)
Michelle Williams, 2006(35 of61)
Open Image ModalIn 2006, Michelle Williams won an Academy Award for her role in Brokeback Mountain wearing a vintage-inspired Vera Wang gown. While some critics disliked the daring saffron hue on her, we think the bold colour – paired with a red lip and soft updo – suited lovely Michelle to a tee. (credit:Kevin Mazur/WireImage)
Geena Davis, 1992(36 of61)
Open Image ModalCreated by costume designers Ruth Meyers and Bill Hargate, Geena Davis’s 1992 “mullet dress” was a bulgy mess. She was nominated that year for her role in Thelma and Lousie, but remembered best for her kooky red carpet look. (credit:WireImage)
Kate Hudson, 2003(37 of61)
Open Image ModalHollywood’s golden girl never looked more radiant. In 2003, Kate Hudson showed up at the Oscars in a sequined Atelier Versace gown, complete with hand sewn lace embroidery and paired with stunning diamond jewelry. Accentuating the look with a relaxed updo and a gorgeous gold clutch, Kate was red carpet perfection. \n (credit:Steve Granitz/WireImage)
Celine Dion, 1999(38 of61)
Open Image ModalThe Canadian-grown diva hit a low note in 1992 with this backward Dior suit. Pairing the baggy, twisted tuxedo with an over-sized fedora and sunglasses, the ridiculous outfit landed our girl on all of the worst-dressed lists that year. (credit:Jim Smeal/Getty Images)
BEST: Penélope Cruz, 2007(39 of61)
Open Image ModalCritics were divided over Cruz’s Versace gown in 2007 – the dramatic look was not for the faint of heart, and yes, there were a lot of feathers – but we think the Spanish actress pulled it off. The pale blush colour looked stunning on her, while a sleek bun kept all the drama on the dress. (credit:Getty Images)
Björk, 2001(40 of61)
Open Image ModalWho could forget the infamous swan dress Björk wore in 2001? The Icelandic singer-songwriter’s feathery costume was universally critiqued and goes down in Oscar history as one of the worst dresses of all time. Props to Björk, however, for achieving such a memorable look– we’re still talking about ‘the swan dress’ over a decade later. (credit:Getty Images)
Hilary Swank, 2005(41 of61)
Open Image ModalIn 2005, Hilary Swank was at the top of her career – and her fashion game. The backless Guy Laroche gown showed off her million dollar body, and quickly became one of the most iconic Oscar dresses of all time – though we’re still wondering how she managed to keep it all in place. (credit:Getty Images)
Tyra Banks, 2000(42 of61)
Open Image ModalThis may have been before her days as a Top Model judge, but Banks should have known better. The shiny purple satin and massive tulle skirt reminds us of bad ‘80s prom dress. (credit:Steve Granitz/WireImage)
Grace Kelly, 1955(43 of61)
Open Image ModalFor the 27th Academy Awards, Grace Kelly donned a mint-green gown by Edith Head, winning Best Actress for her role in The Country Girl while making major waves on the fashion scene. The silk material for the dress alone reportedly cost $4,000, at the time making it the most expensive Oscar dress ever made. (credit:The Kobal Collection/Warner Bros)
Kim Bassinger, 1990(44 of61)
Open Image ModalMore proof that dress-designing should be left to the pros: Kim Bassinger decided to go the DIY route when she showed up to the 1990 Oscars in her own creation – a massive, white satin ball-gown, which she bizarrely paired with a one-armed military jacket. (credit:Ron Gaella/WireImage)
Mila Kunis, 2011(45 of61)
Open Image ModalThis lavender gown looked gorgeous on Mila, who in 2011 opted for a soft, understated look in a year where bold gowns took precedence. The Elie Saab dress’s incredibly low neckline brought some sex appeal to the layers of chiffon lace, while a smoky eye and romantic updo highlighted the Black Swan actress’s natural beauty. (credit:Robyn Beck/AFP/Getty Images)
Gwenyth Paltrow, 2002(46 of61)
Open Image ModalThe usually sleek Gwenyth Paltrow looked uncharacteristically sloppy in this Alexander McQueen dress in 2002, in part due to her decision to leave her bra at home. Raccoon eye makeup – and her terrible posture! – weren’t doing her any favours, either. (credit:Sebastian Artz/Getty Images)
Nicole Kidman, 1997(47 of61)
Open Image ModalFor the 69th Annual Academy Awards, Kidman chose a unique, green-embroidered dress that made her stand out on the red carpet. The haute-couture look marked John Galiano\'s debut at Christian Dior in 1997 -- his first year at the fashion house. (credit:WireImage)
Hilary Swank, 2003(48 of61)
Open Image ModalBeware pink tulle on the red carpet: The Christian Dior ballerina dress Swank wore in 2003 was universally panned by fashion critics for making the Hollywood heavyweight look like a little girl playing dress-up. (credit:Steve Granitz/Getty Images)
Keira Knightley, 2006(49 of61)
Open Image ModalNow this is how you do couture! This shimmery, bourdeux-coloured mermaid gown by Vera Wang embodied all the drama that is The Oscars. A stylish ponytail and bold statement necklace completed the striking look – all without aging the young starlet. \n
Faith Hill, 2002(50 of61)
Open Image ModalFaith Hill couldn’t decide on a dress colour in 2002, so she decided to show up looking like an Easter egg. (credit:WireImage)
Elizabeth Taylor, 1961(51 of61)
Open Image ModalThe violet-eyed beauty snagged a Best Actress win for Butterfield 8 in 1961, and wowed Oscar audiences in a gown that embodied the mega-star’s inimitable style. Pairing a pale yellow top with a flower-embroidered white skirt, she accessorized with a red rose appliqué on her hip, and (of course) a pair of ridiculously decadent pearl and diamond earrings. (credit:Darlene Hammon/Hulton Archie/Getty Images)
Kate Hudson, 2001(52 of61)
Open Image ModalHudson made a fashion blunder in 2001 when she stepped onto the red carpet in this purple Stella McCartney creation. The dress itself wasn’t actually so terrible; rather, bad styling may have been to blame. We could have done without the collared shoulder-piece, the bright fuchsia lipstick, and the poodle-inspired updo. (credit:Getty Images)
Kate Winslet, 2002(53 of61)
Open Image ModalKate put British designer Ben de Lisi on the map when she wore this one-shoulder design with flower detailing at the Academy Awards in 2002. The dress fit Kate like a glove and inspired a succession of one-shouldered red Oscar gowns for years to come. (credit:Chirs Pizello/AP)
Uma Thurman, 2004(54 of61)
Open Image ModalUma looks amazing in almost everything, but this 2004 getup baffled us. Part-pirate, part-peasant girl, the Christian Lacroux gown was a poufy mess that didn’t do the Kill Bill actress justice. (credit:Getty Images)
Cate Blanchett, 2005(55 of61)
Open Image ModalA pale yellow Valentino dress with burgundy accents was a very shrewd choice for Blanchett, who in 2005 took home the Oscar for Best Supporting Actress for her portrayal of Hollywood icon Katharine Hepburn in The Aviator. (credit:Stewart Cook/Rex USA)
Juliette Binoche, 1997(56 of61)
Open Image ModalChanneling the Queen of Hearts in a heavy velvet gown, Juliette Bionche looked anything but regal when she accepted her Oscar for Best Supporting Actress in The English Patient in 1997. She looked more like the bride of Dracula than an Oscar-winner. (credit:Getty Images)
Charlize Theron, 2004(57 of61)
Open Image ModalTheron won Best Actress for her role in Monster in this glittering Gucci gown, proving she was anything but. The slinky dress showed off her amazing curves, while her wavy, old-Hollywood hair was pure glamour. (credit:Getty Images)
Ashley Judd, 2001(58 of61)
Open Image Modal2001 was a bad year for lilac, with Judd trying a bit too hard to channel the 1920s in an unflattering satin dress and piles of jewelry. This flapper-inspired look was a flop. (credit:Michael Caulfield/AP)
Gwenyth Paltrow, 2011(59 of61)
Open Image ModalMinimalism works for Gwenyth -- she positively shined in Calvin Klein at the 2011 Academy Awards. Pops of colour from Louis Vuitton jewelry and simple straight hair complemented the shimmery look. (credit:Getty Images)
Jennifer Connelly, 2002(60 of61)
Open Image ModalJennifer Connelly may have won Best Supporting Actress for a Beautiful Mind, but the dress she wore to the 2002 Oscars was far from beautiful. The layered taupe gown washed out Connelly’s pale skin, and that nonsensical beige scarf made the whole thing just look blah. (credit:Baur Griffin/Wireimages)
Angelina Jolie, 2012(61 of61)
Open Image ModalIt was the leg heard ‘round the world: Angelina Jolie’s jutting pose may have been a bit over-the-top, but it started an Internet frenzy of Twitter handles and animated .gifs dedicated to the glamorous gam. The dark velvet Versace dress will no doubt go down in Oscar history – all because of a little leg. (credit:Getty Images)