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Gwyneth Paltrow's Style Evolution: From Calvin to...Calvin?

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Gwyneth Paltrow is Hollywood royalty—mom is actress Blythe Danner and her late father was director Bruce Paltrow. A shining star in her own right, she began dating Brad Pitt in 1994 and the press went wild for the golden couple. Here they're attending the Waterworld premiere in April of 1995. How conservative does she look in her black dress and Mary Janes?

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24-year-old Gwyneth donned a red velvet suit by pal Tom Ford (then at the helm of Gucci) for the 1996 VMAs. Love the exaggerated cuffs.

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The gorgeous couple attended the 68th Annual Academy Awards in 1996 where Pitt was nominated for his role in 12 Monkeys. Her red matte lip is so '90s and the simple sheath dress reminds us of Carolyn Bessette’s stunning wedding dress. Paltrow was often photographed with a  wrap of some sort—GP loved a pashmina back then, but didn’t we all?

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Paltrow debuted her new shorter ‘do to rave reviews at the Hard Eight premiere in 1997.

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Paltrow’s turn in Shakespeare in Love put her squarely in the spotlight (dating actor Ben Affleck also attributed). She attended the 1999 Golden Globes with long, stick-straight hair extensions and taffeta ballgown skirt from Calvin Klein.

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In 1999 the Best Actress nominee attended the 71st Annual Academy Awards with her father, Bruce Paltrow, in a custom pink Ralph Lauren gown and Fred Leighton jewels.

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The white tweed Chanel suit is killer; the Birkenstocks? Questionable. This was taken in 2002.

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We don’t know if it was marriage to Chris Martin or what, but GP stepped up her fashion BIG TIME in the early 2000s. And why shouldn’t she? She has amazing designer friends and an amazing figure to boot. Here she is wearing Stella McCartney at the 2005 Academy Awards.

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Paltrow glows in this cream Balenciaga gown that accommodates her growing baby bump. Her son Moses was born in April of 2006.

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Paltrow continues to take risks and we love it. She arrived at the 2007 Vanity Fair Oscars party in a blush colored chiffon gown by Zac Posen.

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In 2008, Gwyneth attends the Hottest Pink Party Ever thrown by the Breast Cancer Research Foundation.

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It’s nice to see celebrities letting their hair down. Paltrow attends a 2008 event benefitting charity Baby Buggy in minimal makeup and an easy white frock appropriate for a hot summer day in the Hamptons.

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Paltrow’s hemlines started to rise dramatically in 2008 due to her daily workouts with mega-trainer to the stars, Tracey Anderson. Pal Madonna introduced them. Here she is at a screening of Iron Man wearing a black mini from pal Stella McCartney.

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The actress was on hand to celebrate the release of Valentino: The Last Emperor. The designer and Paltrow are longtime friends, and she donned a strapless black dress from one of his last collections for the label.

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Gwyneth co-hosts a signing party for Valentino: The Last Emperor DVD at VBH Madison Avenue.

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Always ahead of the trends, the stunner wore a lace gown from Antonio Berardi at a dinner to celebrate jeweler Chopard's 150th anniversary.

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At the 2010 CFDA Awards wearing Michael Kors.

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The actress added songstress to her list of talents as she sang at the 2011 Academy Awards. She donned a champagne gown that was gathered at the waist by Michael Kors.

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Paltrow arrived at the 2011 Academy Awards in a metallic column gown by Calvin Klein. She accented the look with jewelry from Louis Vuitton--this one knows what she's doing.

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The actress and mother of two honored her friend Stella McCartney in this stunning column gown at the 2011 Met Ball.

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Always chic, even in the dog days of summer. Gwyneth wears vintage Calvin Klein to a daytime charity event.

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This cobalt dress is jaw-droppingly gorgeous, and we wouldn't expect anything less from Paltrow.

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Paltrow stunned at this year’s Emmys in Pucci that hadn’t even come down the runway yet. Now that’s some serious clout.

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