Cameron Diaz's Best & Worst Looks From Her Iconic Movies

Since her mid-'90s breakthrough, Cameron Diaz has portrayed a wide range of completely different characters. Throughout her career thus far, the star has worn plenty of looks in front of the camera, from delicate red dresses to quirky hooded jackets. In fact, the fashion her on-screen characters have given us has been fabulous in some instances and cringeworthy in others.

Just like the women she has portrayed, Diaz's personal style also has range. Cameron Diaz may have given us plenty of best-dressed moments in her 40s, but that certainly doesn't mean the actor didn't rock some questionable 'fits throughout the years, too. In fact, Cameron Diaz's most inappropriate outfits so far show that, just like most of us, the star has also had some fashion flops. But today, it's not about her personal style, but rather the styles we've seen her embrace on-screen. From a fabulous look in "Charlie's Angels" to an atrocious one in "My Best Friend's Wedding," here are some of the best and worst Cameron Diaz film fashion moments.

In the 1994 comedy "The Mask," Cameron Diaz portrays Tina Carlyle, whose style is absolute '90s perfection. The scene in which Diaz wears a tight red dress with a black floral cardigan still lives rent-free in our minds, as it showcases just how powerful on-screen fashion can be. In fact, the garment is an easy argument for the fact that the little red dress is the new LBD, as it is a timeless choice.

The 1997 rom-com "My Best Friend's Wedding" remains one of Cameron Diaz's most well-known late-'90s hits, as she starred in it alongside fellow it-girl Julia Roberts. In the film. Diaz portrays Kimberly Wallace, whose wedding dress, well ... left plenty to be desired. The bulky silhouette, odd off-the-shoulder sleeves, and dramatic floral embellishments created a look that most wouldn't pick as their big wedding day fashion moment.

"Charlie's Angels" remains a classic early 2000s Cameron Diaz movie that shows just why the actor was one of the era's most successful stars. The film, which preaches about female power, also has some stunning fashion moments, and one Diaz look from the 2000 film that most people instantly think of is the one-shoulder red top and black pants combo. Sexy yet comfortable, the look worked regardless of whether her character, Natalie Cook, was dancing or fighting.

While the red top and beige pencil skirt that Cameron Diaz wore in the 2011 comedy "Bad Teacher" suited the character, the black stiletto heels remain a classic example of why early 2010s fashion hasn't had its return. The mesh shoes, in particular, are what made the character Elizabeth Halsey's look less sophisticated and more tacky. While it served the story, it's not a Cameron Diaz on-screen outfit to draw inspiration from.

The gold bodycon dress that Cameron Diaz's character, Joy McNally, wore in the 2008 comedy "What Happens in Vegas" is a great example of just how stunning metallic fashion can be when done right. The bodycon silhouette suited the star beautifully, and pairing the look with minimal accessories allowed the dramatic fabric to have its moment. While bodycon dresses have gone in and out of style since, the character's take on them showcases just why the silhouette is among the types of dresses everyone should own.

The 2006 Christmas rom-com "The Holiday" is a classic for a reason, and the film's fashion certainly has a nostalgic Y2K flair to it. In it, Cameron Diaz portrays Amanda Woods, who travels from Los Angeles to rural England for the holidays. With that, her cold-weather fashion isn't as stunning as her warm-weather look, and the brown coat she wears upon her arrival in England is definitely a bold choice. The dramatic white lapels distract from the brown fabric, which noticeably clashes with her black pants and pointy heels.

As a shade opposite green and blue on the color wheel, burgundy suits Cameron Diaz particularly well. In the 2001 psychological thriller "Vanilla Sky," Diaz's character, Julianna Gianni, wears a burgundy coat while driving a car, and the color beautifully accentuates the actor's stunning blue eyes — even bringing out the subtle green tones in them. Paired with a maroon scarf, the look is a great example of how one can have fun with colors even when it comes to fall and winter fashion.

In the 2013 crime thriller "The Counselor," Cameron Diaz portrays Malkina, whose style is the epitome of early 2010 trends. In one scene, the character is having drinks at a restaurant while wearing a jacket with metal embellishments decorating the shoulders. While that in itself is dramatic design, the jacket also featured a hood, which the character keeps on throughout her conversation. The look is so unusual that it undeniably contributed to the fact that the scene went viral in September 2026.

In the 2002 rom-com "The Sweetest Thing," Cameron Diaz portrays Christina Walters, whose style is definitely the epitome of noughties fashion. During a clubbing scene, Diaz's character is dressed in a black one-shoulder long-sleeved top and red metallic low-waist statement pants. The simple combination could easily be worn today, especially with plenty of Y2K trends making a major comeback in 2026.

2014's "Annie" is an adaptation of the 1977 Broadway hit, and in the film, Miss Hannigan is portrayed by Cameron Diaz. The film's fashion choices were impeccable, as Hannigan's disheveled and messy looks captured the nature of her character perfectly. But, nonetheless, they remain some of Diaz's on-screen fashion moments we're not too fond of. The layered jewelry, scarves, and fuzzy tops are simply too much for a coherent and cool look.