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At age 9, was already a red carpet regular (following her breakout role in E.T.) – so it was no surprise that she was a pro at getting glam. She wore a gunmetal full-skirt frock with pearls and fur to the 1984 People’s Choice Awards.
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GETTING IT WHITE
From her platinum curls to her pale skin and ivory gown, a 15-year-old Drew projected an aura of innocence at a 1990 party, but things may have been a little wilder below the surface – just a year later, she published her memoir of drug addiction and alcoholism, Little Girl Lost.
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That’s one way to make an entrance! Drew looked ready for takeoff at the 1995 MTV Video Music Awards in a sweetheart-neckline mermaid gown with “wings,” made even more dramatic thanks to dark lips and her signature daisy accessory.
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Ever the style chameleon, Drew opted for super-short fringe and a slinky spaghetti-strap gown (the style was spotted on legions of prom-going girls not long after), plus chunky platform peep-toes, at the 1997 London premiere of Scream.
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ALL THAT GLITTERS
As if we needed any more evidence that the star has always done her own thing! Drew made quite the style statement at the 1998 Oscars, forgoing giant gems and designer gowns for an off-the-rack backless black dress, a few well-placed daisies and a healthy coating of body glitter.
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Proving that she is quite the independent woman at the 2003 Hollywood premiere of Charlie’s Angels 2: Full Throttle, the star complemented co-stars and Lucy Liu in a white suit worn over nothing but a black bikini top.
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THE DARK SIDE
By 2005, Drew had taken every fashion risk imaginable on the red carpet when she turned a chic corner and decided to take style more seriously. She showed it by wearing an embellished black strapless gown with antique-feeling gems and a silver clutch to the Oscars.
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CHARTREUSE WITH ENVY
She’d done wild child, flower girl, skin-baring and elegant, but Drew had yet to give subtly sexy a try – and she pulled it off with ease in a simple celery-green column with an over-the-top embroidered neckline, thigh-high slit and sun-kissed locks at a 2007 Versace event in Beverly Hills.
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Few stars could pull off the mussed hair and voluminous maxi the star sported at the Hollywood premiere of Grey Gardens in 2009, but Drew’s megawatt smile and perfectly coordinated baubles helped make this look lovely, not loopy.
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You were expecting her to stay in one style era? After a brief detour through the groovy ’70s, Drew revisited 1920s fashions in a serious way, wearing a beautifully beaded Deco-inspired nude gown, a birdcage veil and fringed fur at the N.Y.C. Grey Gardens premiere in 2009.
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HAIR SHE IS!
Drew’s dusty blue Dior Haute Couture gown, with its row of buttons and structured skirt, was enough to get tongues wagging. But she took the look to the next level with a larger-than-life bouffant that ended up being one of the 2009 Golden Globe Awards’s most memorable moments.
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HIP TO BE SQUARE
The Grey Gardens love kept coming for the star well into 2010, when she picked up a Golden Globe for best actress. Drew proved she truly was going for the gold in a statuesque Atelier Versace gown with structural crystal embellishments, Lorraine Schwartz diamonds, a Roger Vivier clutch and Jimmy Choo sandals.
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BELT IT OUT
Drew’s Catherine Malandrino gown at the 2010 L.A. Going the Distance premiere was the perfect quirky-yet-chic foundation for her brand new ombré locks – a look that continues to be emulated by women everywhere.
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From Hollywood bad girl to the face of CoverGirl: in 2011, Drew feted the brand’s 50th anniversary in Hollywood wearing a radiant tangerine Jil Sander dress, blonde locks and an understated black clutch.
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