Anne Hathaway's Stunning Style Transformation Over The Years

Anne Hathaway has become a staple of Hollywood, thanks to the decades of hard work that she has dedicated to her craft. Although movies like "The Devil Wears Prada 2" and "The Witches" kept her name in the papers throughout the 2020s, many of her most iconic roles date back to the early 2000s. Indeed, films like "The Princess Diaries" and "Ella Enchanted" were what made Hathaway's career to begin with. Even Hathaway herself looks back at these experiences as transformative. As she told People in 2019 of "The Princess Diaries," "Getting to make it and be on set every day, I got to hug Julie Andrews every day. That part was also very, very, very magical. Then it came out and it was received. That part even, by the way, was magical."

As Hathaway stepped away from these early roles and took on more critically acclaimed parts, her acting skills evolved significantly. Interestingly, her comfort with the fashion world also transformed. If Hathaway started to attend more red carpet events, she also had to select an increasing number of glamorous outfits to fit these occasions. At the beginning of her career, she struggled to choose dresses that were appropriate for Hollywood roles. Over time, though, Hathaway became more comfortable with the rules of fashion — and eventually became a full-blown fashionista. 

These days, Anne Hathaway is known as a Hollywood powerhouse, but back in 2001, she was a small-time actor who had just been launched to overnight fame. Photographs of Hathaway from this time show that she was not necessarily comfortable choosing a wardrobe for the red carpet. At the "Princess Diaries" premiere, Hathaway wore a bland beige strapless dress that did not exactly fit her well. Indeed, the accumulation of large creases around her chest and the small of her back showed that the dress was not necessarily the ideal cut for her body type.

In some ways, Hathaway's early fashion fails are unsurprising. The actor started off her career with a role in the sitcom "Get Real." However, the show only lasted one season, and when it was canceled, Hathaway didn't initially know what to do next. Everything changed for the aspiring star, though, after she landed the lead in the "Princess Diaries" movie alongside the stunning yet tragic Julie Andrews. Hathaway obtained overnight fame in the iconic part and was quickly invited to red carpet events — like the movie's premiere.

On this occasion, Hathaway's choice to wear an ill-fitting dress in a drab color was nothing more than a sign of her inexperience. Fascinatingly, her lack of fashion skills contrasted greatly with the massive success of the film. "I got very, very, very famous," Hathaway later admitted to People.

Anne Hathaway's breakout role in "The Princess Diaries" may have resulted in overnight fame, but the actor initially struggled to develop the corresponding fashion sense. It took time for Anne Hathaway to undergo her stunning transformation from a stylistic newbie to a red carpet pro. As such, when Hathaway started promoting the 2004 film "Ella Enchanted," she made a fashion faux pas that didn't exactly portray her in the most professional light. At one promotional event, Hathaway sported a pink sundress embroidered with white flowers. She paired the frock with a pair of blue jeans. Even more egregiously, she finished the ensemble off with a pair of pointed-toe heels covered in faux gems.

Here, we see Hathaway's lack of fashion experience on full display. While her sundress was totally adorable, it would have paired much better with a pair of strappy heels or some wedge sandals. With their white leather material and pointed-toe style, the shoes she did wear to the event gave off a Wild West vibe that would have been more appropriate for a figure like Dolly Parton than an up-and-coming Hollywood star.

Hathaway's jeans also clashed with her sundress. To remain in dialogue with early 2000s fashion trends, she might have done better to wear them with a tunic and some chunky jewelry. That said, Hathaway's willingness to try out unconventional style pairings also hinted at a search for her own style identity. 

Although Anne Hathaway experienced some early fashion fails, she also enjoyed a few wins. While promoting "The Princess Diaries 2," the actor looked incredibly stylish and on trend. At one daytime red carpet promotional event, Hathaway posed in front of a poster for the movie with a smile on her face and a killer outfit to match. In sharp contrast to her "Ella Enchanted" ensemble, which paired jeans and a dress, Hathaway combined her denim with a trendy black tank. To dress up her look, she sported a semi-transparent half-sleeved cardigan that fell just below her jean pockets. She then belted her top with a black ribbon — a '00s fashion move that totally deserves to make a comeback.

After Hathaway's previous red carpet fails, this outfit was a major win. It showcased Hathaway's ability to engage with the trends of the time, all while maintaining the family-friendly image that got her cast in so many children's films to begin with. Sure, Hathaway's chunky bracelets, heeled sandals, and pink toenails certainly dolled up her look a bit. But none of these elements made her seem like she was desperate for attention. They just made her seem comfortable with the trends of the time. Ultimately, Hathaway's "The Princess Diaries 2" red carpet look showed the world that she was ready to face the cameras and dress like a real movie star.

If "The Princess Diaries 2" showed that Anne Hathaway had gained more confidence in her own style choices, "The Devil Wears Prada" gave her that final push into true Hollywood glamour. When Hathaway was first cast in the iconic movie alongside Meryl Streep, she felt an incredible amount of pressure. Not only would she have to act alongside one of the greatest actors of all time, but she would also be expected to dress incredibly well for red carpet events. In some ways, this was to be expected. The film was, after all, about fashion, and it would be impossible for Hathaway to promote it without being minimally stylish. Nonetheless, Hathaway struggled with these dynamics, later telling People, "I felt so lost when I was 22, which really worked for the character."

Even if Hathaway felt lost at "The Devil Wears Prada" events, she didn't look like a floundering young actor. This was clear at the 63rd Venice Film Festival, where Hathaway was a vision in a white Grecian gown by Alberta Ferretti. After consulting with celebrity stylist Rachel Zoe, Hathaway learned how to lean into movie star glamour. The top-notch styling of Hathaway's couture gown really made her pop among a sea of famous actors and directors. Her choice of outfit showed some of the industry's top players that she was no longer a Hollywood newbie but rather a serious actor with big aspirations.

Anne Hathaway's style transformation truly took off following her iconic role in "The Devil Wears Prada." As she consulted with more wardrobe experts and collaborated with more designers, Hathaway's outfits grew increasingly influenced by the world of haute couture. By the time Hathaway appeared at the 65th Venice Film Festival in 2008, she had transformed into a totally different person, fashion-wise. Dressed in a gray and green ruffled gown by Versace, Hathaway looked like she'd stepped straight off the cover of a fashion magazine. Whereas she had once struggled to select appropriate shoes, Hathaway now wore trendy metallic heels that complemented her color scheme perfectly. Even Hathaway's Bulgari jewels added the right pop of color to her look. The unsure girl from the actor's "The Princess Diaries" days was gone.

Naturally, there was a reason why Hathaway was able to take her style choices to new heights. Since "The Devil Wears Prada" premiere, the actor has been inundated with exciting new projects. She had starred alongside the likes of Dame Maggie Smith in the critically acclaimed historical romance, "Becoming Jane." And, she had also participated in box office winners like "Get Smart." Because of this, by the time she attended the "Rachel Getting Married" premiere at the Venice Film Festival, Hathaway had every reason to feel better than ever about her career. The actor's confidence is what ultimately allowed her to pull off that magnificent Versace gown.

In 2013, everything changed for Anne Hathaway. After appearing in the award-winning film "Les Misérables" the year before, Hathaway brought home a slew of awards. She won a Golden Globe for best supporting actress, a BAFTA for best actress in a supporting role, and a Satellite Award for best actress in a supporting role. The real crown jewel, though, was the Oscar for best supporting actress that Hathaway also won for her part in "Les Mis." And, when she attended the Academy Awards that year, Hathaway dressed like a serious actor who was ready to bring home the industry's most prestigious prize.

For the ceremony, Hathaway wore a gorgeous pale pink gown by Prada. While not quite as attention-grabbing as some of the other dresses that she had worn to previous red carpets, this piece showcased Hathaway's more serious side. The gown's very light shade of pink made her natural skin tones pop, while its minimalist sheath cut accentuated her athletic figure. Interestingly, the dress almost made Hathaway's silhouette mimic that of the Oscar she was about to receive. This visual dynamic was accentuated by the actor's bob haircut, which remained emblematic of her role in "Les Mis." Indeed, the scene in which the professional shaved her own head in front of the cameras resulted in one of Hollywood's most fascinating moments — and one of Anne Hathaway's most dramatic hair transformations yet.

In 2013, Anne Hathaway's wave of acting awards transformed her from a comedic actor into a serious one. No longer was she the star of children's films like "The Princess Diaries" or "Ella Enchanted." She was now an Oscar winner. This natural evolution in Hathaway's career spilled over into her wardrobe. For the first time, Hathaway didn't have to try so hard to stand out fashion-wise. Rather than wearing so many large, frilly dresses, Hathaway leaned into some crisper, bolder looks. She no longer needed to put effort into exuding Hollywood glamour, thanks to the fact that her very name had become quite glamorous.

This was clear at the 2014 Met Gala, where Hathaway appeared in a red two-piece dress by Calvin Klein. The theme of that year's gala was "Charles James: Beyond Fashion" in honor of a designer who was famous for designing elaborate ballgowns. Hathaway's choice to wear a simple scarlet two-piece ensemble to an event where everyone else would be swimming in tulle was, in some ways, shocking. At the very least, it demonstrated her desire to stand out from the crowd, and at most, it indicated a desire to rebel against the establishment. Although Hathaway was ultimately criticized by fashion outlets for departing too much from the theme, her outfit was indicative of her newfound attitude.  No longer did Hathaway necessarily feel obligated to follow the rules of fashion. Instead, she felt open to being bold!

Maternity clothes may not be easy to find, but Anne Hathaway found a way to transform designer couture into peak pregnancy fashion. In 2019, Hathaway was pregnant with her son, Jack Shulman, after having welcomed her eldest child, Jonathon Shulman, three years before. When she showed up at the red carpet for the LA premiere of "Modern Love," Hathaway surprised the crowds by ditching maternity wear altogether. Instead, she looked radiant in a pretty cream Oscar de la Renta dress, which she wore as a top. Although the piece was originally designed to fall on one's upper thigh, Hathaway filled the skirt with her belly, creating a look that was all her own.

To maintain the dressy look established by the Oscar de la Renta piece, Hathaway paired it with a pair of white pants. She then accessorized the look with some strappy sandal heels and ancient Egyptian-inspired jewelry. These stylistic choices placed Hathaway firmly on the list of the best maternity red carpet looks of all time. By wearing an outfit that was not originally designed for pregnant women, Hathaway pushed the bounds of fashion. She showed the world that she could make fashion work for her body — instead of the other way around. 

The COVID-19 pandemic was not necessarily the best time for fashion, but Anne Hathaway managed to make waves anyway. In 2021, while on an outing to Soho House, the actor incidentally brought back some of the top trends from the previous decade. Dressed in a black tunic, sheer black tights, and knee-high boots, Hathaway looked like she'd arrived straight from the 2010s. Her gray overcoat and black scarf matched the energy of her look, and the ensemble made us feel totally nostalgic for that iconic fashion era.

It practically goes without saying that, in this instance, Hathaway's boots were especially spectacular. Her footwear recalled a scene in the original "The Devil Wears Prada" movie, in which her character, Andy, sported a pair of knee-high Chanel boots to the office. Hathaway, as Andy, stunned her colleagues with her spectacular new shoes. One even asked, "Are you wearing the Chanel boots?" — a line which became one of the most iconic lines of the film.

Hathaway's decision to bring back looks from the 2000s and 2010s reminded her fans of the era when she first graced the silver screen. Her outfit stood as a reminder of where she began her career — and how far she had come since. That said, her foundation and lip color were a little off, reminding us of Anne Hathaway's biggest makeup fails. In the end, though, the overall outfit was on point.

As Anne Hathaway's career has progressed, her fashion decisions have changed immeasurably. This is evident in Anne Hathaway's transformation from the first "The Devil Wears Prada" movie to the sequel. While promoting the first movie at the 2006 Venice Film Festival, Hathaway had looked a little unsure in her couture. Two decades later, however, she totally rocked the red tea dress she selected for the 2026 world premiere of the second "Devil Wears Prada" movie. Designed by Nicolas Ghesquière of Louis Vuitton, the dress embraced the bold, unapologetic glamour of the film with its bright red monochromatic fabric. The dramatic corset and structured skirt combo also provided the fashion-forward confidence that Hathaway's character, Andy, came to represent.

If Hathaway's look changed considerably from one film to the other, it's because she evolved as a person in that time. As her co-star, Meryl Streep, told Extra, it was amazing to see Hathaway grow from a budding young actor into an award-winning professional. "So, [Anne Hathaway] was 22. Emily Blunt was 22, I think, when we shot the [first] movie," Streep recalled. "And to come back, and they're grown-ups. They're mothers. They're accomplished, celebrated actors. And just that. Just people with history, and we all brought that, all of our history, into this." Hathaway didn't just contribute her acting experience to the movie, but she also brought two decades of fashion experience on set with her.