10 Rare Fashion Flops From Anne Hathaway

Anne Hathaway has been in the public eye for decades, which means she's been photographed in countless outfits. For someone who's spent so much time in the limelight, it's a bit surprising just how infrequently she's had a worst-dressed list-worthy moment. Of course, not every fashion risk can be a style success — even for a star like Hathaway. Over the years, she has sported some outfits that had us begging her to fire her stylist. 

From award show red carpets to Met Galas and even simply being photographed while walking around outside, Hathaway has sported some looks that had heads turning for all the wrong reasons to all sorts of occasions. While the star of "The Devil Wears Prada" typically has good taste, she clearly enjoys experimenting now and then. And there have been times when those experiments definitely did not have good outcomes. Over the course of her long career, she's exposed body parts that she really shouldn't have, sported strange silhouettes, and went way too trendy with some of her looks in the early aughts. We love a star who isn't afraid to make a fashion statement. Unfortunately, a worst-dressed list appearance or two comes with the territory in that case. 

That's precisely how we collected Hathaway's top 10 worst fashion fails throughout her career.

Anne Hathaway went all out for the 2023 Met Gala, sporting an all-white look with some daring cutouts. The Met Gala is certainly the place for a fashion statement. This look, however, was a swing and a miss. The safety pin-inspired details and big, stitch-like cutouts looked haphazard, overly busy, and a little like the costume of a horror character, Paired with her done-up beehive-esque hairstyle, she was radiating Bride of Frankenstein vibes, and that felt like a bit of an odd choice for this big event.

In 2013, Anne Hathaway met a career milestone most actors only dream of. She attended the 85th Academy Awards and went home a winner, earning the Best Supporting Actress award for "Les Miserables." Unfortunately, her look for the evening wasn't a winner. Her satiny dress nearly perfectly matched her skin tone. Its straight-up-and-down silhouette paired with her pixie cut left her looking a bit like a monochromatic tube, while some unfortunate seams on the bust left many folks wondering if the dress was a bit see-through.

This wasn't Anne Hathaway's first flop of a Met Gala outfit, and it likely won't be her last. Even so, she was among the worst-dressed celebs at the 2025 Met Gala with this interestingly incoherent ensemble. The voluminous collared shirt and body-skimming, horizontal striped maxi skirt had totally clashing vibes. While it probably still wouldn't have been our favorite look, seeing the skirt extended into a matching top probably would've made this a 'fit better. As it was, though, it looked casual and all wrong for the special occasion.

Anne Hathaway first arrived on the scene in the early aughts, and at the time, she didn't shy away from the trends of the moment. Of course, some of those trends don't look nearly as cool now as they once did. Still, that doesn't change the fact that what she wore to "The Lord of the Rings: The Two Towers" premiere in 2002 was a downright bad 'fit. The white suit, too-long pants, and bizarrely long scarf — everything about this look was a mistake, leaving her looking washed-out and oddly proportioned.

Perhaps Anne Hathaway thought she looked like a gift when she attended the 79th Academy Awards in this bow-adorned lace gown back in 2007. Unfortunately, this look was a total mess. It almost looked as if someone tacked a few black bows on a wedding dress to make it appropriate for an award show. Ultimately, the black bows clashed with the rest of the look, and they still didn't manage to stop this white lace, mermaid-style gown from resembling a bridal moment.

While promoting "The Odyssey" in August 2026, Anne Hathaway wore an outfit that got some negative attention. Fans noticed she was wearing her jumpsuit backwards; the higher neckline in the back was meant to go in the front. Hathaway even addressed the fashion moment, noting that it was, in fact, an accident. Interestingly, though, there wasn't anything wrong with wearing this piece backward. It was the jumpsuit, itself, with its odd silhouette and bizarre flowy details, that made this 'fit a flop.

We're all for going braless. but this ensemble was certainly an interesting choice. Anne Hathaway left little to the imagination at the 2003 premiere of "School of Rock" with a sheer, long-sleeve frock. It's hard to imagine why Hathaway chose to sport this 'fit to the premiere of a kids' movie, of all things. Beyond that, this just wasn't a good look. The dress had a strange silhouette and the shade clashed with her boots. So, even if she'd layered with the necessary slip, this still wouldn't have been one of her best looks. 

If a fashion show isn't the place to take a fashion risk, then what is? It's hard to argue with this logic, but it's also hard to defend the all-black look Anne Hathaway sported at Versace's Fall/Winter 2023 show. This shiny, crocodile skin, sculptural mini-dress was a total miss all on its own. Yet Hathaway styled an already busy garment with too many statement-making accessories. The heavy patent leather boots, the oversized sunglasses, the little black bag, the jewels: it's hard to comprehend what she was going for here.

In August 2026, Anne Hathaway attended the Los Angeles premiere of "The End of Oak Street" in an ensemble that got quite a bit of attention online for a reason she likely didn't anticipate. Her low-rise jeans and high-low top exposed her baby bump in a particularly unusual way. This left many fans questioning whether hers was a real baby bump at all. She defended her pregnant belly on Instagram, joking, "Fake hair, real bump." It's clear, though, that this outfit was an odd look either way.

Anne Hathaway wore all black to a "Chicago" screening in 2002. While this color palette typically makes for a safe look, this dress wasn't Hathaway's best statement. This ensemble certainly wasn't the worst of the worst, but it definitely wasn't a winner, either. The placement of the belt detailing, paired with the way the fabric fell, hugged her body in a way that didn't quite work and created a strange silhouette. Paired with simple hair and makeup and a black, closed-toe pump, nothing about this look felt properly planned.