Explore Anne Hathaway’s boldest fashion moments from the 2000s, including red carpet highlights and daring looks that set the tone for years.Anne Hathaway, amfAR and ACRIA Honor Herb Ritts. Photography: Getty

Anne Hathaway has been captivating the silver screen since the early 2000s, shortly after she began her acting career.

Across roles such as The Princess Diaries (2001), Ella Enchanted (2004), and The Devil Wears Prada (2006), she proved her acting prowess and penchant for style. A lot of her characters had great wardrobes, too. Hathaway has spoken about being grateful for her role in The Princess Diaries because it helped jumpstart her career. As it progressed, so did her style. During the 60th Golden Globe Award in 2003, Hathaway’s Spring 2004 Haute Couture dress by Elie Saab became a pivotal moment in her own fashion journey.

The Devil Wears Prada, a highly fashion-forward film, showcased many outfits from her looks running around Manhattan delivering coffee to Chanel boots in the office. These ensembles still live on mood boards for people beginning their first corporate jobs or looking for overall inspiration. Her fashion choices have set trends and resonated with young women, inspiring them to express their individuality and confidence. We are particularly interested in her most daring looks. Take, for instance, the nude-hued Vera Wang dress she wore in 2005 at a Stephen Sondheim Birthday Celebration.

Hathaway’s choices offer a masterclass in how to be versatile between understated elegance and bolder looks. Keep scrolling to discover L’OFFICIEL‘s round-up of Hathaway’s most daring looks.

1 / 19Anne Hathaway, at The 60th Annual Golden Globe Awards, 2003. Photography: Getty