Anne Hathaway’s presence on the red carpet has often divided both fans and critics, with her fashion choices drawing praise for bold risks, while sometimes triggering visible disappointment. From the early 2000s press run for “The Devil Wears Prada” to the most recent Met Gala, Hathaway’s evolving style has consistently captured the public’s attention. Over the years, she has delivered a mix of jaw-dropping hits and surprising missteps, each moment scrutinized under the bright lights of Hollywood world premieres, award ceremonies, and fashion’s biggest nights. Her journey—marked by iconic transformations, risky ensembles, and candid admissions—provides a rich tapestry for discussion, especially for those caught between admiration and doubt.
Hathaway’s first encounter with the fashion elite began innocently. Unlike her iconic character Andy Sachs, she approached the world of couture with genuine excitement.
she confessed in a 2006 interview, highlighting the genuine joy she felt in experimenting with style. Yet her passion was met with fashion’s trademark fickleness: after blessing audiences with regal “Princess Diaries” ensembles and the daring Chanel-inspired looks of “The Devil Wears Prada,” Hathaway herself landed not only on best-dressed lists but, at times, on those notorious compilations of fashion misfires.
Recalling the downside of such public scrutiny, Hathaway once found herself on a worst-dressed list for an outfit she thought “was very nice.” The memory became bittersweet when she discovered her grandmother had saved the critical article as a keepsake.
Hathaway said, trying to embrace the turbulence that comes from being a global style figure.
One of Hathaway’s earliest and most talked-about red carpet slips occurred at the 2006 Screen Actors Guild Awards, where she celebrated a nomination for her work in “Brokeback Mountain.” Determined to project a more mature image after leaving her princess days behind, Hathaway wore a two-toned Nina Ricci gown combining whispery lace, soft velvet, and delicate chiffon. However, the odd pairing of baby blue with black overwhelmed her fair skin, and a shimmery band of fabric curved awkwardly across her midsection, disrupting the silhouette. This attempt at romance fell flat, with the young actress admitting even years later that she was “still learning” the art of style.
The same year, during the French premiere of “The Devil Wears Prada” at the Deauville American Film Festival, Hathaway’s fashion sense faltered once again. Rather than channeling the high-octane glamour of the movie’s fashion-centric world, she arrived in a basic black dress marred by a gold waistband and rosette—often compared to a cheap award ribbon. Not even silver earrings and plain pumps could save the unremarkable look, which drew more shrugs than gasps. Still, Hathaway’s growth was evident, as she gradually transitioned from such forgettable outfits toward bolder, more sophisticated choices.
Not all of Hathaway’s fashion experiments fell into mediocrity. By the time of the 2023 Met Gala, she had mastered the fine art of red carpet drama, donning a show-stopping Chanel-inspired ensemble that paid homage to Elizabeth Hurley’s famed safety pin dress. The risk paid off, earning her high marks on numerous best-dressed lists—for once, fashion’s mercurial tastes bowed in her favor.
Despite the triumphs, Anne Hathaway knows the sting of critique all too well. At the 79th Academy Awards, she stepped out in a sleeveless Versace gown, its elaborate black bows and wedding-dress silhouette meant to impress. Instead, critics compared her ensemble to cartoonish holiday décor, with the oversized bows overwhelming her slender frame and the skirt’s fit appearing ungainly. The attempt at festive grandeur only underscored that even the biggest nights can end in style regret. Yet Hathaway’s honesty about her struggles was ever apparent:
she admitted at the time. Such admissions resonated with aspiring fashion fans who saw both grit and vulnerability in their idol.
The 2013 Oscars marked a turning point—not just for Anne Hathaway’s career, but her place in fashion discourse. Accepting the Academy Award for Best Supporting Actress in “Les Misérables,” Hathaway wore a blush Prada column gown whose construction would forever overshadow her victory. Social media and late-night shows exploded with jokes about the dress’s darts and the illusion of “nipplegate.” Hathaway later revealed she’d switched to the Prada at the last minute, after learning another star would wear a similar Valentino.
