Anne Hathaway Looks That Had Heads Turning For All The Wrong Reasons

During her press run for "The Devil Wears Prada," Anne Hathaway revealed that, unlike her character, Andy Sachs, she entered the insular fashion world free from apathy. "I think fashion is a lot of fun. I love clothes," she told MovieWeb in 2006. Unfortunately, fashion hasn't always loved Hathaway back. In fact, its fickleness has landed her on a few worst-dressed lists.

Hathaway has blessed her fans with countless iconic looks both on- and off-screen. There's her regal wardrobe in "The Princess Diaries," her modern take on Catwoman's catsuit in "The Dark Knight Rises," her period pieces in "Becoming Jane," and her fashion girlie garb in "The Devil Wears Prada" — including those aspirational Chanel boots. Hathaway's fashion sense has also turned her on to some red carpet hits, including her 2023 Met Gala ensemble. She took a real risk by giving Elizabeth Hurley's sexy safety pin dress a sophisticated Chanel makeover and was rewarded with appearances on several best-dressed lists.

However, it was how Hathaway felt about landing on the opposite end of a fashion publication's red carpet rankings that she discussed with Vogue in 2023. "I remember wearing an outfit that I still think was very nice, and I wound up on the worst-dressed list," she recalled. When she saw her grandmother had saved a clipping of the list, the actor was able to look at the negative assessment of her outfit in a different light. "Even when it's terrible, it's great," she said of her style mantra. Perhaps one of the rare red carpet misfires here is the one of which her grandmother was so proud.

Anne Hathaway left her princess era behind when she joined the cast of Heath Ledger and Jake Gyllenhaal's groundbreaking contemporary Western about a tragic clandestine romance between two cowboys. Hathaway wanted her role in "Brokeback Mountain" so badly that she lied to get it, and her dishonesty paid off when she and her co-stars earned a Screen Actors' Guild Awards nomination for best cast in 2006. Perhaps the "Ella Enchanted" star's goal was to look more mature when she attended the SAG Awards that year, as she was getting recognized for taking on a more adult role. However, her two-toned gown looked like a messy mashup of two items you might find in a film for mature audiences only: a negligee and silk sheets.

The whispery lace, soft velvet, flowy silk, and delicate chiffon that had been pieced together to create Hathaway's Nina Ricci dress would have radiated romance — if only the material were one color. The pairing of baby blue and black washed her out, although the latter would have been complementary to her fair skin on its own. Unfortunately, there was a lot more of the shimmery blue on display, including a band of fabric that curved down underneath the bust. It sliced across the dress's silhouette to further upset the balance of ill-matched materials.

While musing on why moviegoers find makeover montages like her royal glow-up in "The Princess Diaries" so mesmerizing, Hathaway told Vogue, "I think we all love growth." So, it wasn't necessarily a bad thing that she still had a lot of growing to do in her fashion journey at this point in her career.

One secret about Anne Hathaway's casting in "The Devil Wears Prada" is that she wasn't even in the top five most-wanted actors for the role of Andy Sachs, the recent college grad who lands a job working for the intimidating editor-in-chief of Runway magazine. Hathaway was far more thrilled to get hired than her character was, recalling to Variety, "I had some buddies over. I remember running out in my living room, half dressed, screaming — I got 'The Devil Wears Prada!'" Considering the film's fashion-conscious premise, you'd think Hathaway would have killed on the red carpet while promoting it. However, there was no slayage when she attended the movie's 2006 French premiere at the Deauville American Film Festival.

When choosing her garb for the event, Hathaway didn't even try to go for the gold — but she did wear a tacky band of gold fabric around her waist, while a rosette transformed it into a cheap award ribbon. The only contest she could've won was for the most basic little black dress. Her silver earrings clashed with the glittery gold embellishment, and a pair of plain black pumps did nothing to elevate the ensemble. The dress would have been "meh" without the metallic addition, which created an "X" on her lower midsection that all but eliminated the garment's flattering shape by drawing the eye away from its fitted waist. Yet, while this look might have hindered Hathaway's stunning transformation into a style star, she would eventually find her fashion footing.

Two years before Anne Hathaway faced off against Kate Hudson in their 2009 comedy "Bride Wars," she almost looked ready to walk down the aisle at the 79th Academy Awards. Countless designers have determined that adding big bows to dresses makes them more aesthetically interesting. Unfortunately, this resulted in the red carpet being oversaturated with the festive flourish, and Hathaway fell prey to the allure of the sartorial cliché. If Miranda Priestly were to lay eyes on the look, she might say, "Giant bows on the red carpet? Groundbreaking."

Hathaway's bows looked like Wednesday Addams' idea of holiday décor and they were attached to a bland wannabe wedding dress. Hathaway actually could have benefited from a bigger front bow in this instance, as the top half of the dark decoration gave the illusion of a narrower bust. The fit of her sleeveless Versace gown's skirt also appeared a bit off, likely because it was gathered low in the back where another goth bow straight out of Hot Topic's "The Nightmare Before Christmas" collection bobbed about behind her as she walked the red carpet.

While "The Devil Wears Prada" taught Hathaway a lot about the business side of fashion, she knew she still had so much to learn at this stage in her life. "Style, for me, is something I still can't get right," she admitted to Zap2it (via The Ledger) in 2006.

The devil was in the details of this Prada look. No one could see past those darn darts when Anne Hathaway showed up to the 85th Academy Awards in the blush column dress. Headlines about Hathaway's best supporting actress win were drowned out by pieces about her outfit's distracting structural elements and the direction the discourse drifted definitely wasn't where she wanted it go. Today tackled the topic by turning a terrible dad joke into a headline reading, "Les Nipplerables? Hathaway's dress draws attention." Mocking Hathaway's gown also became the internet's new favorite pastime, with one X user joking, "Anne Hathaway's nipples have nipples."

Hathaway told USA Today that she chose the Prada dress just two hours before she hit the red carpet, explaining why she had to make the last-minute decision in a statement to People. "It came to my attention late Saturday night that there would be a dress worn to the Oscars that is remarkably similar to the Valentino I had intended to wear," she said. Her statement also included an apology to Valentino.

Hathaway could have avoided the whole hullabaloo by wearing her original pick and having a laugh with her red carpet twin. Instead, the "Les Misérables" star had to add one more thing to her list of stuff to feel miserable about on her big night. "It looked like my nipples were hard, I had full blown laryngitis and had to sing, and a bunch of corny haters were getting lots of attention," she wrote on Instagram. But, at least she got to leave the event with an awesome new gold accessory.

From the neck up, Anne Hathaway looked lovely at the 2016 Toronto International Film Festival, where she attended the premiere of her movie "Colossal." However, everything below that was a colossal mistake. With lace tiers, oddly shaped floral patchwork appliques, and beaded trim, her Rodarte dress looked like something a crafty grandmother might construct. One look at her and just know that somewhere in her closet there's a Danish cookie tin containing thread, buttons, and one of those tomato-shaped pincushions.

To make matters worse, her sheer long sleeves made her arms appear larger, while the volume and length of her skirt, combined with the ankle strap on her heels, shaved inches off her legs (or at least it appeared that way). Her shoes were also black, a color that did not feature in her frou-frou frock at all. At least Hathaway didn't have to worry about another celeb copying her look on the red carpet, and a valuable lesson she learned from her "The Devil Wears Prada" character was applicable to her long, arduous fashion odyssey. She told New York Magazine, "Even if it's going to be a slow climb, she finds that's better than if you shoot up stratospherically and meteorically, just to be a copy of someone else."

After her Oscar win, Anne Hathaway's haters became so vocal that they actually started to affect her livelihood. "A lot of people wouldn't give me roles because they were so concerned about how toxic my identity had become online," she told Variety. Hathaway credited director Christopher Nolan with reinvigorating her career by casting her in his 2014 sci-fi drama "Interstellar." Perhaps she was still having a hard time finding a stylist willing to work with her when she attended the movie's New York premiere, though.

Some dresses break the mold, but Hathaway broke out the mold for the event. Her dress was such a bizarre blend of fabrics, with one side looking like black lace with dead ivy creeping over it and the other resembling blue cheese. In addition to being shot through with moldy veins, the garment was bulky and shapeless, and its asymmetrical hem with eyelash lace just further overloaded a confusing, cluttered look. But please don't hate the Hathaway; hate the gamble she took on this head-scratcher of a look.

It might be cliché to compare dresses to drapery, but this voluminous mass of taffeta is what you might get if Catwoman got tangled up in the Vatican's red curtains while trying to filch a few of its treasures during the conclave. However, instead of claws, Anne Hathaway had those dangerous-looking spikes jutting from her hair. She was engulfed in way too much fabric, and those flaps at the neck of her frock resembled a sad, limp bow. Her window dressing, with a narrow sternum window was the work of Pierpaolo Piccioli for Valentino Haute Couture.

The Vatican had to be on "The Idea of You" actor's mind when she was planning this look for the 2018 Met Gala, as the theme that year was "Heavenly Bodies: Fashion and the Catholic Imagination." Hathaway courted controversy by attending the event, which some critics viewed as being sacrilegious. One witness later complained to Page Six about the way Hathaway was posing for photos taken by her husband, Adam Shulman. "Anne was sitting there like she thought she was a saint ... She was acting as if she was Jesus," sniffed the unidentified observer. However, after she learned that her brother was gay, Hathaway actually left the Catholic Church due to its stance on homosexuality, so perhaps she didn't view her behavior as blasphemous. "Why should I support an organization that has a limited view of my beloved brother?" she said in an interview with British GQ.

Anne Hathaway couldn't decide whether she wanted to channel a pop star partying in a casual look or a sophisticated business mogul managing a consulting firm in a power suit when she appeared on "Good Morning America" in 2023. The jarring juxtaposition of blue jean material and a lightweight black fabric was obviously the point of this Dion Lee design, but sometimes thinking outside the box results in outfits that are more odd than innovative.

The denim-on-denim corset and bottom combo just doesn't feel like Hathaway's aesthetic — it's more the vibe of Taylor Swift cheering for Travis Kelce on game day. The effect here was of a torso floating in a black void, and on Hathaway's spliced top, the seam joining the denim to the thinner black fabric was crooked, making her bust look uneven. Her bottoms' pants-over-pants design also made her crotch look weirdly long. "I never thought I'd see the day when I got Julia Fox-inspired vibes from an Anne Hathaway GMA appearance," read one Redditor's review of the look, which actually would have been a pretty chic pantsuit without the denim disruption around her midriff.

Okay, if Miranda Priestly saw this outfit, she definitely wouldn't have to deliver that famous cerulean sweater speech to Anne Hathaway, and perhaps she wouldn't tell the "Alice in Wonderland" star she possesses zero fashion sense. Hathaway's 2024 SAG Awards look was almost sartorially sound; her silver sandals and skirt with a high thigh slit were both elements that worked and her crop top was pretty close to being perfect with its molded cups, wide V-neck, and gravity-defying, off-the-shoulder sleeves. Unfortunately, her much-too-wide matching belt demolished her "The Devil Wears Prada" homage.

Instead of simply nodding to the film by sporting its signature color, Hathaway could have fit a photograph of her and Meryl Streep in character on the movie's set inside that frame-sized silver buckle. Apologies to Versace, but supersizing various accents feels like a lazy way to make something feel high fashion. (Remember those black bows?) And while wide belts can be slimming, Hathaway was wearing hers a bit low, which actually made her torso appear shorter.

While it wasn't Hathaway's best Versace look, Priestly would be (silently) proud of the relationship she has built with the respected fashion house. "I am very excited to work for a company that wants to have [a] 40-year-old woman as their face. ... I love to work with people who love you back, and it's amazing to be seen by people who are looking for someone like you," Hathaway told Women's Wear Daily in 2024.

While she stuck to the "Superfine: Tailoring Black Style" theme by paying homage to late Vogue editor André Leon Talley, Anne Hathaway made the worst-dressed list for the 2025 Met Gala with her hodgepodge of aesthetics that didn't quite mesh. It looked like she'd raided the kingdom of Genovia's crown jewels when choosing her accessories; the centerpiece of her look wasn't an impeccably tailored piece but a bulky Bulgari necklace featuring a massive sapphire surrounded by diamonds.

The rest of the actor's outfit felt dull in comparison to the positively regal necklace's ornate design; if its blue jewel were the nose of a blue blood, it would have sniffed in derision at everything below it. Hathaway's white shirt with billowing sleeves was giving Disney prince when he's keeping it casual so at least there was that. But there was a complete disconnect between the bold black and silver stripes on Hathaway's crystal-encrusted column skirt and the rest of her ensemble. While it wasn't bad enough to wear to a hideous skirt convention, one Redditor opined, "This is just boring and uninspired."

Hathaway's outfits can't all be hits, but they always include a little something special that gives her a red carpet radiance no jewels, shimmery fine fabrics, or sparkly embellishments can compete with. "What do I wear to feel confident? For me, confidence begins with gratitude," she told Vogue. And her fans will always be grateful for the opportunity to gaze upon her style statements, no matter which list they wind up on.