Inappropriate Outfits We Can't Believe Anne Hathaway Wore

It felt like Anne Hathaway had become Hollywood's most hated celeb by the time she won her 2013 Oscar for her work in "Les Misérables," and the pale pink dress she wore to the event gave her "Hathahaters" something else to sneer at. But according to Hathaway, those disastrous darts that made her gown look a bit inappropriate weren't part of her original outfit plan.

The New York Times distilled the essence of the internet hate for Hathaway down to people finding her earnest, overly enthusiastic, and inauthentic. Then there was the PR mess surrounding her 2013 Oscars dress. Before the event, Valentino confirmed that Hathaway would be wearing one of their designs. So, when the diva wore Prada instead, it seemed that she had snubbed Valentino. Hathaway later explained to Harper's Bazaar that she had to nix her first gown choice because it had already been worn to an event, and she discovered too late that the Valentino she had settled on instead was strikingly similar to the Oscars dress her "Les Misérables" co-star Amanda Seyfried had picked out. When Hathaway tried on her last resort on the day of the event, she recalled telling her husband, "It looks like my nipples are hard."

At least she got to experience one of the highest points of her life while wearing that dress; she didn't have an Oscar to console herself with when she suffered some of her other serious sartorial stumbles.

Anne Hathaway has undergone a stunning transformation since charming viewers as Crown Princess Amelia Mignonette Thermopolis Renaldi. Her makeover moments in "The Princess Diaries" and "The Devil Wears Prada" are also some of the most magical metamorphoses committed to film. Unfortunately, Hathaway didn't actually have Julie Andrews or Meryl Streep as stern fairy godmothers because she certainly could have used some advice from the Queen Regent of Genovia or Miranda Priestly before she got dressed for the 2004 premiere of "Ella Enchanted."

Hathaway embraced an early aughts trend by wearing flared jeans underneath a pink tunic dress. The dress featured a smattering of embroidered white flowers. Over it, she wore a green-and-white coat with a floral pattern. It was giving the cushions of grandma's dining room chairs, which made for some major disharmony between it and the more youthful, Bohemian style of her dress. She completed her look with white pointy-toe heels and a green handbag. All of the style elements were just too overwhelming — the combo was as cursed as Hathaway's "Ella Enchanted" character.

The actor's jeans were also a bit too casual for a premiere. By contrast, her co-stars Parminder Nagra and Vivica A. Fox wore stylish dresses that were modern takes on princess gowns. Luckily, Hathaway eventually left the Y2K era behind — "The Idea of You" star tells Vogue that she now looks to Gen Z for style inspo. ""It's a fun generation when it comes to fashion," she said.

While promoting "Ella Enchanted" in 2004, Anne Hathaway spoke to LiveAbout about her plans to move on from princess roles. "[I'll] go off and play all the drug addicts and the prostitutes, and all the good ones you win Oscars for a little bit later on. But now I am, yes, ready to hang up the tiara [and] put the ball gown in storage." With the tragic prostitute role that won Hathaway her Oscar came experimentation with an edgier look.

For the 2012 NYC premiere of "Les Misérables," Hathaway wore a black Tom Ford gown with a high slit on the side to showcase her bondage-style footwear. Unfortunately, she didn't wear underwear with her outfit — a detail disclosed when a photographer snapped a photo of her exiting her vehicle ahead of the event. A Daily News headline about the incident screamed "The Devil Wears Nada!" while the Calgary Herald scolded Hathaway, advising her to "Put on some underwear."

While going commando with that particular dress proved to be a regrettable move, Matt Lauer's remarks to Hathaway on "Today" were far more inappropriate. "Nice to see you," he said in greeting. "Seen a lot of you lately." This forced Hathaway to address the incident. After shaming the photog who sold the NSFW photo of her wardrobe malfunction, she said, "I'm sorry that we live in a culture that commodifies sexuality of unwilling participants."

Many celebrities use the Met Gala as an opportunity to step outside their comfort zones and wear outfits that would be considered too extravagant and avant-garde for typical red carpets. But in 2014, Anne Hathaway didn't deviate from the status quo when she showed up at the Metropolitan Museum of Art in a two-piece Calvin Klein ensemble. It featured a strapless crop top and a column skirt with a front slit. Its candy apple red color, which almost perfectly matched the red carpet, was the most exciting thing about it.

Hathaway's outfit was an especially poor choice for that particular year because the theme was "Charles James: Beyond Fashion." James was a designer who specialized in crafting exquisite ball gowns, so it would have been an excellent time for Hathaway to revisit her princess era.

During a 2019 appearance on "The Late Show," Hathaway revealed an even bigger issue with the dress — it was a bit too tight. "I was about a block away from the Met ... and I sneezed and my dress split," she recalled. When she arrived at her destination, she told the dress' designer, Francisco Costa, what had happened. "I've never actually seen someone turn green before," she continued, revealing that Costa refused to let her walk inside holding her dress together. By a stroke of luck, they found a seamstress at a nearby hotel who was able to repair the damage.

Miranda Priestly would be so mortified by Anne Hathaway's awkward encounter with designer Donatella Versace at Versace's Fall/Winter 2024 show. Hathaway was wearing a Versace design, obviously, but she should have conducted a mobility test before meeting with Donatella while rocking the red leather mini-dress. 

The "Interstellar" star treated her Instagram followers to a video of her failed attempt to sit beside the designer on a couch. Hathaway only made it halfway there — she seemingly couldn't bend her torso and had to prop herself up on a throw pillow. "I just want to respect the integrity of the corset," Hathaway joked. All poor Donatella could do was laugh while the actor writhed around and demonstrated a serious design flaw in her fashion house's garment. Donatella also begged for someone to help Hathaway get back up. "No! I'm fine, I'm fine," Hathaway assured her. "It's for Donatella!" At least the two women were laughing the entire time this went down.

While the dress wasn't the most practical of garments, Hathaway's video was a hit with her fans. "I love when women do this. We all talk about how wonderful the pics from the red carpet look, but oftentimes the dresses are so uncomfortable or borderline impossible to wear, being open about it is refreshing," one Redditor wrote. Meanwhile, another person wondered how one would use the restroom in such a tight-fitting 'fit. "So many questions!" they wrote.

For the "She Came to Me" premiere at the 2023 Berlin Film Festival, Anne Hathway wore a sheer mesh Valentino dress with a 3D bow motif. She accessorized with black opera-length gloves, and underneath her gown, she wore a nude bodysuit. Tom + Lorenzo observed that the bodysuit gave Hathaway an unfortunate case of "Barbie crotch." "At this point, why not just line the dress?" they asked. The bodysuit also flattened her chest, creating an odd disconnect between her visible legs and the lack of definition up top.

However, Hathaway has learned that there's something to be said about the value of flesh-colored undergarments. In a 2022 piece for Interview, she told Marc Jacobs that one of her biggest fashion regrets is skipping her bra for an event. "[I] did not know my dress was see-through ... It was a very long carpet, and at no point did any of the people in that wall of photographers stop to give me a heads-up or offer me a jacket," she said. Hathaway was likely talking about the black dress she wore to the "School of Rock" premiere in 2003; most photos of it are NSFW.

Perhaps Hathaway's naked dress missed the mark, but it does fit with the style aesthetic she has adopted. She told The Hollywood Reporter, "I was introduced to the world as a teenaged princess, but I never actually connected to things that are 'sweet' and 'pretty' — no shade at all for those wonderful options. I love the right risk."