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.