See How Maggie Gyllenhaal Went From Donnie Darko to Indie Style Icon
Photo: Dimitrios Kambouris/Getty Images
Known for her roles that celebrate complicated women in both blockbuster films and indie flicks, Maggie Gyllenhaal has become a champion for the dynamic woman. Starting her career in the 2000 film Donnie Darko alongside her brother Jake Gyllenhaal, she’s since grown out of supporting roles and become an indie icon. A vocal advocate for women’s rights, Gyllenhaal has spoken out about issues like ageism and the willingness to embrace female imperfections.
As one would expect, her sense of style is just as dynamic as her career. Gravitating toward clean lines with ornate details, she is as likely to be seen in an Oscar de la Renta gown as a Monse shift. From a sequinned Marni set to a caped, graphic Valentino gown to a Victorian Gucci frock, her style maintains a sense of humor and avoids trends.
See all of her best looks, from walking the red carpet alongside her brother for Donnie Darko until now, in our slideshow ahead.
May 1, 2017 Where: At the 'Rei Kawakubo/Comme des Garcons: Art Of The In-Between' Costume Institute Gala at Metropolitan Museum of Art in New Yor...
May 1, 2017 Where: At the 'Rei Kawakubo/Comme des Garcons: Art Of The In-Between' Costume Institute Gala at Metropolitan Museum of Art in New York City. What: Outfit by Marni.
Photo: Karwai Tang/WireImage
March 8, 2017 Where: At the BE BOLD FOR CHANGE panel event in celebration of International Women's Day in New York City. Photo: Paul Zimmerman/W...
March 8, 2017 Where: At the BE BOLD FOR CHANGE panel event in celebration of International Women's Day in New York City. Photo: Paul Zimmerman/WireImage
February 18, 2017 Where: At the closing cerimony of the 67th Annual Berlinale International Film Festival in Berlin. Photo: Rune Hellestad - Cor...
February 18, 2017 Where: At the closing cerimony of the 67th Annual Berlinale International Film Festival in Berlin. Photo: Rune Hellestad - Corbis/Getty Images
February 14, 2017 Where: At the premiere of 'Beuys' during the 67th Annual Berlinale International Film Festival in Berlin. Photo: Dominique Cha...
February 14, 2017 Where: At the premiere of 'Beuys' during the 67th Annual Berlinale International Film Festival in Berlin. Photo: Dominique Charriau/WireImage
February 9, 2017 Where: At the premiere of 'Django' during the 67th Annual Berlinale International Film Festival in Berlin. Photo: Stephane Card...
February 9, 2017 Where: At the premiere of 'Django' during the 67th Annual Berlinale International Film Festival in Berlin. Photo: Stephane Cardinale - Corbis/Corbis via Getty Images
February 8, 2017 Where: At a photocall during the 67th Annual Berlinale International Film Festival in Berlin. Photo: Sean Gallup/Getty Images
January 4, 2017 Where: At the 2017 National Board of Review Gala in New York City. Photo: Dimitrios Kambouris/WireImage
July 17, 2016 Where: At the 'Love: From Cave To Keyboard' by Pepsi Exhibition Opening in New York City. Photo: Mark Sagliocco/FilmMagic
February 18, 2016 Where: At the Marc Jacobs show during New York Fashion Week Fall/Winter 2016. Photo: Jamie McCarthy/Getty Images for Marc Jaco...
February 18, 2016 Where: At the Marc Jacobs show during New York Fashion Week Fall/Winter 2016. Photo: Jamie McCarthy/Getty Images for Marc Jacobs
January 10, 2016 Where: At the 73rd Annual Golden Globe Awards in Los Angeles. Photo: Steve Granitz/WireImage
November 30, 2015 Where: At the 25th Annual Gotham Independent Film Awards in New York City. Photo: Gary Gershoff/WireImage
September 20, 2015 Where: At the 67th Annual Primetime Emmy Awards in Los Angeles. Photo: John Shearer/WireImage
September 20, 2015 Where: At the AMC, BBC America, IFC and Sundance TV Emmy After Party in Los Angeles. Photo: Mike Windle/Getty Images for AMC ...
September 20, 2015 Where: At the AMC, BBC America, IFC and Sundance TV Emmy After Party in Los Angeles. Photo: Mike Windle/Getty Images for AMC Networks
September 18, 2015 Where: At the Variety and Women In Film Annual Pre-Emmy Celebration in Los Angeles. Photo: Jon Kopaloff/FilmMagic
June 8, 2015 Where: At the Stella McCartney Resort 2016 Presentation in New York City. Photo: Kevin Mazur/Getty Images
May 31, 2015 Where: At the 5th Annual Critics' Choice Awards in Los Angeles.
Photo: Jason LaVeris/FilmMagic
May 30, 2015 Where: At the 8th Annual Veuve Cliquot Polo Classic in New Jersey. Photo: Dimitrios Kambouris/Getty Images for Veuve Clicquot
May 19, 2015 Where: At the 40th Anniversary Gracies Awards in Los Angeles. Photo: Michael Tran/FilmMagic
May 4, 2015 Where: At the 'China: Through The Looking Glass' Costume Institute Benefit Gala at the Metropolitan Museum of Art in New York City. ...
May 4, 2015 Where: At the 'China: Through The Looking Glass' Costume Institute Benefit Gala at the Metropolitan Museum of Art in New York City. Photo: Jamie McCarthy/FilmMagic
February 24, 2015 Where: At the 2015 ELLE Style Awards in London. Photo: Karwai Tang/WireImage
February 23, 2015 Where: At the Burberry Prorsum show during London Fashion Week Fall/Winter 2015. Photo: David M. Benett/Getty Images for Burberry
January 25, 2015 Where: At the 21st Annual Screen Actors Guild Awards in Los Angeles. Photo: Axelle/Bauer-Griffin/FilmMagic
January 11, 2015 Where: At the 72nd Annual Golden Globe Awards in Los Angeles. Photo: Steve Granitz/WireImage
October 30, 2014 Where: At 'The Real Thing' Broadway Opening Night in New York City. Photo: Bruce Glikas/FilmMagic
July 31, 2014 Where: At a 'Good Morning America' taping in New York City. Photo: Ray Tamarra/GC Images
July 21, 2014 Where: At the premiere of 'Very Good Girls' in New York City. Photo: Andrew Toth/FilmMagic
June 12, 2014 Where: At the Women In Film Crystal + Lucy Awards in Los Angeles. Photo: Jason LaVeris/FilmMagic
June 8, 2014 Where: At the 68th Annual Tony Awards in New York City. Photo: D Dipasupil/FilmMagic
May 7, 2014 Where: At the Christian Dior Cruise 2015 show in New York City. Photo: Rabbani and Solimene Photography/WireImage
May 5, 2014 Where: At the 'Charles James: Beyond Fashion' Costume Institute Gala at the Metropolitan Museum of Art in New York City. Photo: Dimi...
May 5, 2014 Where: At the 'Charles James: Beyond Fashion' Costume Institute Gala at the Metropolitan Museum of Art in New York City. Photo: Dimitrios Kambouris/Getty Images
May 5, 2014 Where: At the 'Charles James: Beyond Fashion' Costume Institute Gala after party in New York City. Photo: Ray Tamarra/GC Images
April 7, 2014 Where: At the MIPTV 2014 Opening Party in Cannes. Photo: Tony Barson/FilmMagic
February 16, 2014 Where: At the 2014 EE British Academy Film Awards in London. Photo: Dave J Hogan/Getty Images
February 5, 2014 Where: At the Rachel Comey presentation during New York Fashion Week Fall/Winter 2014. Photo: Gary Gershoff/Getty Images
September 12, 2013 Where: At the fragrance launch of Estée Lauder 'Modern Muse' in New York City. Photo: Gilbert Carrasquillo/FilmMagic
June 26, 2013 Where: At Gotham Magazine's celebration for its Maggie Gyllenhaal cover in New York City.
Photo: Eugene Gologursky/Getty Images fo...
June 26, 2013 Where: At Gotham Magazine's celebration for its Maggie Gyllenhaal cover in New York City.
Photo: Eugene Gologursky/Getty Images for Gotham Magazine
June 25, 2013 Where: At the premiere of 'White House Down' in New York City. Photo: Jamie McCarthy/Getty Images
June 21, 2013 Where: At the premiere of 'White House Down' in Washington D.C. Photo: Paul Morigi/WireImage
May 6, 2013 Where: At the Costume Institute Gala for the 'PUNK: Chaos to Couture' exhibition at the Metropolitan Museum of Art in New York City. ...
May 6, 2013 Where: At the Costume Institute Gala for the 'PUNK: Chaos to Couture' exhibition at the Metropolitan Museum of Art in New York City. Photo: Kevin Mazur/WireImage
April 30, 2013 Where: At the Catherine Martin And Miuccia Prada Dress Gatsby Opening Cocktail in New York City. What: Dress by Prada. Photo: Ste...
April 30, 2013 Where: At the Catherine Martin And Miuccia Prada Dress Gatsby Opening Cocktail in New York City. What: Dress by Prada. Photo: Stefanie Keenan/Getty Images for Prada
September 23, 2012 Where: At the premiere of 'Won't Back Down' in New York City. Photo: Rob Kim/Getty Images
September 15, 2011 Where: At the Guess Portrait Studio during the 2011 Toronto International Film Festival. Photo: George Pimentel/WireImage
May 2, 2011 Where: At the the 'Alexander McQueen: Savage Beauty' Costume Institute Gala at The Metropolitan Museum of Art in New York City. Phot...
May 2, 2011 Where: At the the 'Alexander McQueen: Savage Beauty' Costume Institute Gala at The Metropolitan Museum of Art in New York City. Photo: Larry Busacca/Getty Images
February 3, 2011 Where: At the 'Three Sisters' Off-Broadway play opening night after party in New York City.
Photo: Bruce Glikas/FilmMagic
May 3, 2010 Where: At the Costume Institute Gala Benefit to celebrate the opening of the 'American Woman: Fashioning a National Identity' exhibit...
May 3, 2010 Where: At the Costume Institute Gala Benefit to celebrate the opening of the 'American Woman: Fashioning a National Identity' exhibition at The Metropolitan Museum of Art in New York City. Photo: Larry Busacca/Getty Images
March 7, 2010 Where: At the 82nd Annual Academy Awards in Los Angeles. Photo: Jeff Kravitz/FilmMagic
March 5, 2010 Where: At the 25th Annual Film Independent Spirit Awards in Los Angeles. Photo: Jon Kopaloff/FilmMagic
February 25, 2010 Where: At 2nd Annual Character Approved Awards in New York City. Photo: Charles Eshelman/FilmMagic
January 17, 2010 Where: At the 67th Annual Golden Globe Awards in Los Angeles. Photo: Frazer Harrison/Getty Images
October 5, 2009 Where: At the premiere of 'An Education' in New York City. Photo: Patrick McMullan/Patrick McMullan via Getty Image
January 11, 2009 Where: At the 66th Annual Golden Globe Awards in Los Angeles. Photo: George Pimentel/WireImage
November 10, 2008 Where: At the MoMa Film Benefit Gala in New York City. Photo: George Napolitano/FilmMagic
July 14, 2008 Where: At the premiere of 'The Dark Knight' in New York City. Photo: Dimitrios Kambouris/WireImage
June 3, 2008 Where: At the 2008 CFDA Awards in New York City. Photo: Patrick McMullan/Patrick McMullan via Getty Image
February 25, 2007 Where: At the 79th Annual Academy Awards in Los Angeles. Photo: Steve Granitz/WireImage
February 28, 2005 Where: At the Vanity Fair Oscar Party in Los Angeles. Photo: Patrick McMullan/Patrick McMullan via Getty Image
January 10, 2005 Where: At the 10th Annual Critics' Choice Awards in Los Angeles. Photo: Gregg DeGuire/WireImage
December 13, 2004 Where: At the Chrismahanukwanzakah Party hosted by Virgin Mobile and Fonzworth Bentley in New York City. Photo: Lawrence Lucie...
December 13, 2004 Where: At the Chrismahanukwanzakah Party hosted by Virgin Mobile and Fonzworth Bentley in New York City. Photo: Lawrence Lucier/FilmMagic
January 26, 2004 Where: At the 61st Annual Golden Globe Awards in Los Angeles. Photo: Michael Caulfield Archive/WireImage
January 19, 2003 Where: At the 60th Annual Golden Globe Awards in Los Angeles. Photo: Frank Trapper/Corbis via Getty Images
January 14, 2003 Where: At the 2002 National Board of Review Awards Gala in New York City.
Photo: Tom Kingston/WireImage
September 26, 2002 Where: At the 2002 IFP New York Gotham Awards. Photo: Jim Spellman/WireImage
October 22, 2001 Where: At the premiere of 'Donnie Darko' in Los Angeles. Photo: Gregg DeGuire/WireImage
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