Style & Beauty

Gwyneth Paltrow's Style Evolution, From Grunge To Goop

Birkenstocks, braless moments, Brad Pitt and more.

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
Ron Galella via Getty Images
With mother Blythe Danner at the fourth annual New York Cabaret Benefit for the Williamstown Theater Festival on April 14, 1985.
1993
Ron Galella, Ltd. via Getty Images
At the premiere of "Flesh and Bone" in Hollywood, California, on Nov. 4, 1993.
1994
Ron Galella via Getty Images
With director James Ivory at the 66th annual Academy Awards on March 21, 1994.
1995
Ron Galella, Ltd. via Getty Images
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
Ron Galella, Ltd. via Getty Images
With Brad Pitt at the premiere of "The Pallbearer" in New York on April 28, 1996.
Circa 1997
Jim Smeal via Getty Images
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
Jim Smeal via Getty Images
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
Jeffrey Mayer via Getty Images
At the 71st annual Academy Awards in Los Angeles on March 21, 1999.
1999
SGranitz via Getty Images
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
Frank Micelotta Archive via Getty Images
At the 74th annual Academy Awards on March 24, 2002.
2002
UK Press via Getty Images
Arriving at a rehearsal in London on April 23, 2002.
2002
J. Vespa via Getty Images
At the Venice Film Festival in 2002.
2002
Bertrand Rindoff Petroff via Getty Images
At a Christian Dior party in Paris in 2002.
2003
Evan Agostini via Getty Images
At the Music Has Power dinner in New York on Dec. 1, 2003.
2004
Dave M. Benett via Getty Images
At the premiere of "Sky Captain and the World of Tomorrow" in London on Sept. 27, 2004.
2005
Carlo Allegri via Getty Images
At the 77th annual Academy Awards in Hollywood, California, on Feb. 27. 2005.
2007
Michael Tran via Getty Images
At Comic-Con in San Diego on July 28, 2007.
2007
Rabbani and Solimene Photography via Getty Images
At a Unicef benefit in New York on Feb. 6, 2007.
2008
Serge BENHAMOU via Getty Images
At the premiere of "Two Lovers" in Paris on Nov. 4, 2008.
2009
Gregg DeGuire via Getty Images
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
Stephan Schraps via Getty Images
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
Neilson Barnard via Getty Images
At the Golden Heart Gala in New York on Oct. 15, 2012.
2012
Kurt Krieger - Corbis via Getty Images
At the 84th annual Academy Awards in Los Angeles on Feb. 26, 2012.
2012
Kevin Mazur via Getty Images
At the 2012 Met Gala in New York on May 7, 2012.
2013
Lars Niki via Getty Images
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
Luca Teuchmann via Getty Images
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
Anadolu Agency via Getty Images
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.