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7 of Anne Hathaway's most iconic outfits

The Princess Diaries star was Y2K royalty in boho dresses and bootcut jeans. Now, she's Queen of Cannes.

by Zoë Kendall
27 May 2022, 7:00am

All images courtesy of Getty Images

The Anne-naissance is upon us. In the early aughts, Anne Hathaway was America’s de facto teen princess, starring as endearing teen royal Mia Thermopoulis in 2001’s The Princess Diaries. By the late aughts, she was playing the equally beloved Andy Sachs opposite Meryl Streep’s icy editrix in The Devil Wears Prada and starring in pop culture juggernauts like Brokeback Mountain and The Dark Knight. At the turn of the 2010s, no thanks to one ill-fitting Prada dress and one too-earnest acceptance speech, the public (unduly) turned its back on the actress.

Nevermind the ‘Hathahaters’, Anne’s always been a queen in our eyes. Sartorially, too. Back in her Diaries days, the actress was a bona fide teen queen in sweet boho dresses, candy-coloured tube tops, snarky slogan tees and a few memorable layered looks involving bootcut denim. By the late 00s (with the ever-chic The Devil Wears Prada under her belt), she was being outfitted by Rachel Zoe and accepting Oscars in Prada. And today, she’s touring the French Riviera looking like a modern-day Audrey Hepburn in custom Armani. In honour of Anne’s stunning turn at Cannes, we’re taking a look back at some of the star’s most iconic outfits across the years.

In The Princess Diaries, 2001

Anne made her Hollywood breakthrough in Y2K classic The Princess Diaries. In the movie, she won our hearts as Mia, an unassuming high school student who discovers she’s the heir to a royal throne. Throughout the film, Mia’s style undergoes a complete 180 (requisite makeover montage et al.) from bookish schoolgirl in spectacles and pleated skirts to polished princess in this gorgeous tiara’d ballgown look.

anne hathaway wearing a purple floral dress at an amfar gala 2002
Photo by Ron Galella/Ron Galella Collection via Getty Images

At an amfAR gala, 2002

At the beginning of her career, Anne made a name for herself playing sweet girl-next-door types. Of course, there was The Princess Diaries’ awkwardly charming Mia, but there was also the obedient Ella Enchanted and the doting daughter in Nicholas Nickelby. Here, Anne wears a look as saccharine as her teen queen reputation: a boho floral dress, straw tote and tiny pink slingbacks.

anne hathaway wearing a striped tube top and white pants at the premiere of 2 fast 2 furious in 2003
Photo by Jon Kopaloff/FilmMagic

At the premiere of 2 Fast 2 Furious, 2003

There’s something about this outfit that makes it so viscerally 00s. Maybe it’s the colour combination (one stripe away from rastafarian), the drawstring-ed tube top, the white boot cut trousers or the beaded strap on that teensy purse. Either way, we’re here for it.

anne hathaway on the teen choice awards red carpet wearing a fed up graphic t-shirt 2004
Photo by Gregg DeGuire/WireImage

At the Teen Choice Awards, 2004

Y2K was the era of the clapback T-shirt, and in 2004, Anne joined the tee’s celebrity fanclub (Paris, Britney, et al.) when she wore this cheeky FedUp tee to the Teen Choice Awards.

In The Devil Wears Prada, 2006 

The scene that launched a thousand memes. Is Anne Hathaway wearing the Chanel boots? Yeah, she is. In 2006, Anne starred opposite Meryl Streep in the much-loved fashion rom-com The Devil Wears Prada. As Andy, Anne plays assistant to Meryl’s Miranda Priestly, the icy editor-in-chief of Runway Magazine. Throughout the film, as she climbs the Runway ranks, Andy undergoes a complete style makeover. One day, she’s being picked apart for wearing a frumpy cerulean sweater, the next she’s wearing — you guessed it — the Chanel boots.

anne hathaway with her academy award wearing a pink prada dress in 2013
Photo by Steve Granitz/WireImage

At the Academy Awards, 2013

In 2013, Anne accepted an Academy Award for her turn as Fantine in movie-musical Les Misérables. Not so much of a winner that evening was Anne’s pale pink Prada gown. The dress caused a stir among fashion critics and casual viewers (and even earned Anne a spot on Time’s Worst Dressed list) due to a pair of poorly placed darts that drew attention to the actress’ nipples. According to Anne, the dress was a last-minute sub in for a Valentino gown that had been pulled for another attendee. In a 2019 Instagram post, the actress addressed the dress (and the Hathahaters), writing, “I had to change my dress last minute and so it looked like my nipples were hard […] and a bunch of corny haters were getting lots of attention from the media for being haters but you know what? It was still the best.” Get em, Anne!

anne hathaway on the red carpet in cannes wearing a trailing custom armani privee gown 2022
Photo by Daniele Venturelli/WireImage

At Cannes Film Festival, 2022

Enter the Anne-naissance. The actress re-claimed her crown on the 2022 Cannes Film Festival red carpet, stunning Twitter in a stunning custom Armani Privé column gown. No longer the princess of Genovia, Anne was proclaimed this year’s queen of Cannes.

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7 Iconic Outfits