Gwyneth Paltrow’s style is like Madonna: constantly in a state of reinvention and best, if you ask us, in the ’90s. There was brunette Gwyn, matching with Brad Pitt Gwyn, wearing a totally off-theme outfit to the Met Gala Gwyn, jumpsuit of your nightmares Gwyn, Goop Gwyn ― the list goes on.
When she’s not making headlines for Goop’s medical claims, the princess of polarization routinely does for her sartorial pursuits, whether iconic, like her 1999 Ralph Lauren Oscars gown, or memeworthy, like the walk seen ’round social media at the 2019 Emmys.
In honor of her 47th birthday on Sept. 27, along with the premiere of her delicious-looking show “The Politician,” premiering on Netflix the same day, take a look back at some of her best fashion moments over the years.
1985
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With mother Blythe Danner at the fourth annual New York Cabaret Benefit for the Williamstown Theater Festival on April 14, 1985.
1993

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At the premiere of “Flesh and Bone” in Hollywood, California, on Nov. 4, 1993.
1994

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With director James Ivory at the 66th annual Academy Awards on March 21, 1994.
1995

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With Brad Pitt at the opening night of “Hamlet” on Broadway in New York on May 2, 1995.
1995

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With Brad Pitt at the premiere of “Copycat” in 1995.
1996

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At the premiere of “From Dusk Till Dawn” in Los Angeles in 1996.
1996

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With Brad Pitt at the premiere of “The Pallbearer” in New York on April 28, 1996.
Circa 1997

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Walking with Winona Ryder.
1997

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With Brad Pitt at the premiere of “The Devil’s Own” in New York in 1997.
1997

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In an amazingly ’90s coat circa 1997.
1998

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At the “Great Expectations” premiere in Los Angeles in 1998.
1998

Ron Galella, Ltd. via Getty Images
At the “Shakespeare in Love” premiere in New York on Dec. 3, 1998.
1999

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At the 71st annual Academy Awards in Los Angeles on March 21, 1999.
1999

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At “The Talented Mr. Ripley” Los Angeles premiere on Dec. 12, 1999.
1999

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At the Metropolitan Museum of Art in New York in 1999.
1999

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At the opening of LVMH Tower in New York on Dec. 8, 1999.
2000

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At the 25th annual Toronto Film Festival in Toronto in 2000.
2000

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At the 72nd annual Academy Awards in Los Angeles on March 26, 2000.
2000

Ron Galella, Ltd. via Getty Images
At the 57th annual Golden Globe Awards in Beverly Hills, California, on Jan. 23, 2000.
2001

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At the 2001 VH1/Vogue Fashion Awards.
2001

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At the Tony Awards in New York on June 3, 2001.
2002

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At the 74th annual Academy Awards on March 24, 2002.
2002

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Arriving at a rehearsal in London on April 23, 2002.
2002

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At the Venice Film Festival in 2002.
2002

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At a Christian Dior party in Paris in 2002.
2003

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At the Music Has Power dinner in New York on Dec. 1, 2003.
2004

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At the premiere of “Sky Captain and the World of Tomorrow” in London on Sept. 27, 2004.
2005

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At the 77th annual Academy Awards in Hollywood, California, on Feb. 27. 2005.
2007

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At Comic-Con in San Diego on July 28, 2007.
2007

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At a Unicef benefit in New York on Feb. 6, 2007.
2008

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At the premiere of “Two Lovers” in Paris on Nov. 4, 2008.
2009

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At a benefit for women’s cancer research in Beverly Hills, California, on Feb. 10, 2009.
2010

Jon Kopaloff via Getty Images
At the 44th annual CMA Awards in Nashville, Tennessee, on Nov. 10, 2010.
2011

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At the Bambi Award ceremony in Wiesbaden, Germany, on Nov. 10, 2011.
2011

Donato Sardella via Getty Images
At the 63rd annual Emmy Awards in Los Angeles on Sept. 18, 2011.
2012

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At the Golden Heart Gala in New York on Oct. 15, 2012.
2012

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At the 84th annual Academy Awards in Los Angeles on Feb. 26, 2012.
2012

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At the 2012 Met Gala in New York on May 7, 2012.
2013

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At the Met Gala in New York on May 6, 2013.
2014

Axelle/Bauer-Griffin via Getty Images
At the 2014 amfAR Inspiration Gala in Los Angeles on Oct. 29, 2014.
2015

NBC via Getty Images
On “The Tonight Show With Jimmy Fallon” on Jan. 14, 2015.
2015

Jeffrey Mayer via Getty Images
At the 87th annual Academy Awards in Hollywood, California, on Feb. 22, 2015.
2015

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At the 49th Golden Camera awards in Berlin on Feb. 1, 2014.
2015

Jon Kopaloff via Getty Images
At the 25th annual EMA awards in Burbank, California, on Oct. 24, 2015.
2016

Donato Sardella via Getty Images
At the Hollywood Reporter and Jimmy Choo’s Power Stylists dinner in Los Angeles on March 15, 2016.
2016

Jason LaVeris via Getty Images
At the LACMA Art+Film Gala in Los Angeles on Oct. 29, 2016.
2016

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At the Elle 30th anniversary party in Madrid on Oct. 26, 2016.
2017

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At the Met Gala in New York on May 1, 2017.
2018

Nicholas Hunt via Getty Images
At the Guggenheim International Gala Dinner in New York on Nov. 15, 2018.
2019

Dia Dipasupil via Getty Images
At the Met Gala in New York on May 6, 2019.
2019

Kevin Winter via Getty Images
At the 71st Emmy Awards in Los Angeles on Sept. 22, 2019.
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