Cameron Diaz’s Best Red Carpet Looks Ever: All the Times She Won Best Dressed

Don’t call it a comeback, though Cameron Diaz has officially returned to the red carpet, making her first appearance on the crimson carpet on Wednesday, January 15, after taking a ten-year hiatus from Hollywood.

When he stepped out for the Berlin premiere of his new Netflix movie Back to Workshe turned heads in a full Gucci look with a decidedly relaxed twist that fit right in with her eternally cool California girl aesthetic. She ditched high heels in favor of Gucci penny loafers that underpinned dark denim mom jeans and sheer blouses, then threw an oversized coat on top for an extra layer of swagger.

But former model Diaz, 51, has always been a red carpet standout, and her celebrity peers have long praised her directional style, a unique brand of poetic bohemia that consistently sets her apart.

In her Vogue May 2003 cover story, Diaz’s Charlie’s Angels costar Lucy Liu she says of her friend’s wardrobe: “For Cameron, it’s an art form, and it’s about transformation and change – like turning a skirt into a tube top. Something could cost $10 or $10,000 – either way, if she’s comfortable with it. She makes it work. She defines her own fashion, and people follow it.”

During her rise to fame in Hollywood, her red carpet aesthetic read like a masterclass in ’90s-era minimalism. She was a fan of little black to all-black dresses that showed off her mile-long legs and would add kicking red heels to simple black pants with a halter top and a cardigan draped over her shoulders. She loved a jacket hat, midriff crop top and lots (and lots) of blue eyeshadow – looks that would feel right at home on today’s Gen-Z style stars.

As she landed bigger roles, she sometimes landed on the worst dressed list. At the 2002 Academy Awards she wore an Emanuel Ungaro Haute Couture kimono dress that is now considered ahead of its time.

“Cameron was a collaborator. She was always open to mixing designers. She looked beautiful in clothes and it was a pleasure. Cameron was ahead of everyone,” her stylists at the time, Clare a I have a Hallworthhave said. “She wore what felt right.”

More than 20 years later, repeating some of her best styles is proof that Diaz is always a red carpet winner. Below, look back at 17 of our favorite Diaz moments, from 1997 My Best Friend’s Wedding New York City film premiere of “Poiret: King of Fashion” Costume Institute 2007 benefit at the Metropolitan Museum of Art.