Julia Stiles' Best & Worst Looks From Her Iconic Movies

Actor Julia Stiles got her big break in 1999 when she starred alongside the late Heath Ledger in "10 Things I Hate About You." After making waves as the extremely stylish Kat Stratford, in the early 2000s, Stiles quickly became a fashion icon who was known for her distinct characterization and wardrobe. In recent years, Stiles' starring roles have continued to provide fashion inspiration. From her edgy outfits featuring camo prints and tube tops in "10 Things I Hate About You" to her low-waisted pants and floral shirts in "The Prince and Me," Stiles proved she could embrace any aesthetic. Despite pulling off more androgynous styles as a female lead in the early aughts, Stiles also wore satin slip dresses that perfectly captured the era's red carpet style.

While reminiscing about Julia Stiles' complete style transformation in an interview with TODAY in 2020, she hinted that her personal style wasn't so different from her "10 Things I Hate About You" costumes. "I was really into chokers in that era," she said [1:29]. However, her style evolution hasn't come without its regrets. "Oh yeah ... cargo pants. Why?" Stiles asked herself while reflecting on her outfits in "Save the Last Dance." [3:02]

While her roles have showcased everything from athletic ensembles to styles that transcend the modern-day, in "Mona Lisa Smile," Stiles' best-dressed moments haven't come without their hurdles. From style clashes to missed opportunities, she's also worn some pretty outdated looks that haven't exactly stood the test of time. Let's review her best and worst looks in movies.

In "10 Things I Hate About You," Julia Stiles arrived at prom as Kat Stratford wearing another remarkably different ensemble. But this time, it was her best. She wore an elegant lavender gown and a regal bun that has continued to inspire formal looks in recent years. Filmed in 1999, Stiles' timeless gown exuded minimalist glamour trends that dominated the era's red-carpet style. While bold silhouettes and crystal accessories were also major fashion trends, subtle slip dresses also made waves in fashion. Her barely-there brows also reflected another one of the trends people actually found attractive in the aughts.

When Julia Stiles took on the role of feminist Kat Stratford in "10 Things I Hate About You," she could hardly have imagined that the role would turn her into an on-screen fashion icon. However, while her leather jackets and tube tops have continued to make waves in fashion, her cozy green cardigan, paired with a floral skirt and tailored trousers, wasn't one of her finest fashion moments. The vibrant color palette of her outfit was a stark departure from her other grunge-inspired ensembles, and the array of hues only emphasized the clash of styles.

Julia Stiles' best outfit in "Save the Last Dance" seamlessly blended bohemian and hip-hop aesthetics. She wore a matching red vest and a bandana that featured a paisley print that nodded toward 1970s-inspired hippie style. However, by pairing her bandana with a pendant necklace and oversized hoop earrings, she channeled a hip-hop-inspired allure. Hip-hop fashion was very much on the rise in the early 2000s, and by blending psychedelic patterns with street dance culture, Stiles helped prove just how versatile the style could be. Her face-framing tendrils were also very 2000s.

During her hip-hop lesson scene in "Save the Last Dance," Julia Stiles was dressed in black cargo pants and a red-and-black raglan T-shirt. Raglan T-shirts became a major fashion trend that dominated street style in the 2000s. However, despite wearing such a stylish T-shirt, Stiles' outfit didn't make the T-shirt the focal point. In fact, the dark trousers even made it blend seamlessly. Attention was drawn downward instead, toward her colorful high-top sneakers featuring burgundy, blue, and white. What's more, the chunky silhouette of her sneakers also completely clashed with her elegant ballet-bun hairstyle.

In 2003, Julia Stiles appeared as college student Joan Brandwyn in "Mona Lisa Smile." With the film set in the early 1950s, Stiles got to experiment with a more vintage take on fashion. Her best look included a relaxed button-up shirt with a beige waistcoat and a dainty pearl necklace. Stiles' appearance mirrored that of Marilyn Monroe. While her elegant string of pearls, particularly when paired with her cherry-red lipstick, reflected the Old Hollywood glamour aesthetic prevalent in the 1950s, Stiles' tailored garments put a powerful spin on her look.

Julia Stiles' worst look in "Mona Lisa Smile" was when she wore a plaid waistcoat with a gray trench and a formal bun. Not only did the look lack her 1950s bombshell aesthetic, but the moody color palette of her ensemble was also a far cry from the powerful ensemble she wore in her introduction at the beginning of the film. Rather than drawing attention to her elegant pearl choker, her cream shirt now concealed it. She accessorized with a floral neckerchief, which was a complete style clash with her green-and-gray plaid waistcoat.

Julia Stiles proved she could be both a princess and a college student when she appeared as Paige Morgan in "The Prince and Me" in 2004. Before the palace gowns and crowns, Stiles was dressed in low-waisted flares, red sneakers, and a black T-shirt. While her vibrant sneakers added a pop of color, the overall muted color palette of her look nodded to '90s minimalism, an early aughts and 1990s fashion trend that has come back in style. The deep V-neck of her black T-shirt highlighted her lack of accessories and made her look effortlessly stylish.

Imagine finding out that your boyfriend is, in fact, a prince. But now imagine arriving at the palace wearing a plum floral shirt. Not great! Unfortunately for Julia Stiles, her worst look in "The Prince and Me" came in what was meant to be one of the most romantic scenes. In true Paige Morgan style, she wore few accessories, which centered all attention on her bold purple blouse. While her plum shirt was not terrible, it felt slightly outdated and mature compared to her trendier outfits in the film.

When Julia Stiles wasn't dressed in uniform as Nicky in "The Bourne Supremacy," she was incredibly stylish. On one occasion, she wore a distinctly early 2000s-inspired outfit that turned an intense scene into one of her best fashion moments. Stiles was dressed in a tailored purple jacket, statement earrings, and a colorful skinny scarf. Skinny scarves were a major fad in the early 2000s, and while Stiles' scarf wasn't particularly narrow, it sure was small enough to be tightly wrapped around her neck.