Maggie Gyllenhaal was the indie darling of 00s cinema — and 00s it girl-dom. The actress began her career as a teenager, appearing (quite memorably) in 2001’s Donnie Darko before making her breakthrough with iconic erotic rom-com Secretary. Since, Maggie’s gone on to star in hits on both ends of the Hollywood spectrum — auteur-led films like Adaptation and mega-blockbusters like The Dark Knight — and has even gone behind the camera, earning Oscar nominations for her directorial debut The Lost Daughter.
And yet to say that Maggie was the indie darling of the 00s it girls is to say that her stellar style was — and remains — criminally underrated. Take the Chanel LWD she wore to the 2003 Golden Globes. Mega chic. The real lily she wore, tucked behind her ear, to the premiere of Secretary? Genius. Balletcore at the 2004 Oscars? Chef’s kiss. Not to mention Maggie was one of the first Miu Miu muses, a predecessor to the many it girls who continue to face the label to this day. Here, we look back at 7 iconic outfits that prove Maggie had — and still has — ‘it’.
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At the Secretary premiere, 2002
After playing supporting roles in cult flicks like Donnie Darko, Maggie made her breakthrough in 2002’s Secretary. In the film, Maggie plays Lee, secretary to demanding lawyer E. Edward Grey (played by who else but James Spader) as the duo’s relationship goes from professional to, well, sadomasochistic. To the film’s premiere, the actress wore this understated black lace dress with a fresh lily behind her ear. A true stroke of style genius.
At the Golden Globes, 2003
Following her star-making turn in Sundance favourite Secretary, Maggie attended the 2003 Golden Globes wearing an appropriately twee Chanel couture AW02 dress along with a very Y2K baguette purse.
At the Independent Spirit Awards, 2003
Did you say “going out”? To the 2003 Independent Spirit Awards, Maggie wore not only an itsy-bitsy party dress, but the era’s ubiquitous “going out” bolero and jewel-tone pumps.
At the Oscars afterparty, 2004
Like any it girl worth her salt, Maggie’s style was eons before its time. Nearly 20 years, to be exact. To the 2004 Oscars afterparty, the actress wore a chiffon dress that would be considered balletcore by today’s standards.
At a party for Louis Vuitton, 2004
Pairing a lamé “going out” top with sailor pants? Very few could pull it off. But Maggie did. Here, she attends a party for Louis Vuitton wearing a mix-and-match, head-to-toe look from the house’s SS04 collection.
For Miu Miu AW04, 2004
A Miu Miu campaign is basically an it girl rite of passage. So, of course, Maggie starred in her own for the label’s AW04 collection.
At the Academy Awards, 2022
In 2021, Maggie made her directorial debut with The Lost Daughter. The film — which she directed and adapted — earned her the Venice Film Festival’s Golden Osella award along with an Oscar nomination for Best Adapted Screenplay. Here, at the 2022 Oscars, the newly-minted director wears a gown from Schiaparelli, one of the year’s buzziest brands. Yup, Maggie’s still got ‘it’!