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 she stepped out for the Berlin premiere of her new Netflix film Back in actionshe turned heads in a full Gucci look with a decidedly laid-back twist that was right in line with her eternally cool California girl aesthetic. She ditched high heels in favor of Gucci penny loafers that grounded dark denim mom jeans and a see-through blouse, 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 celebrities have long praised her directional style, a unique brand of poetic bohemianism that consistently sets her apart.

In her Vogue May 2003 cover story, Diaz’s Charlie’s Angels costs Lucy Liu said 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 — whatever, if she’s comfortable with it. She gets it to work. She defines her own fashion and people follow it.”

Related: Cameron Diaz drops high heels at the 1st premiere after a 10-year hiatus

Cameron Diaz slayed in her highly anticipated red carpet. Diaz, 52, walked the red carpet for the Berlin premiere on Wednesday, January 15, of her new film Back in Action. The actress stunned in an all black ensemble. The outfit included a black blouse with sheer coverage over the top of her torso. Diaz paired the top (…)

During her mercurial rise in Hollywood, her red carpet aesthetic read like a master class in ’90s minimalism. A fan of all-black little black dresses that highlighted her mile-long legs, she added a kicking red heel to simple black trousers with a halter top and a cardigan draped over her shoulders. She loved a cool hat, a midriff-baring crop top, and lots (and lots) of blue eyeshadow — looks that would feel right at home on Gen-Z style stars today.

As she got bigger roles, she occasionally ended up 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 the outfit and she was a delight. Cameron was ahead of everyone,” her stylists at the time, Clare and Nina Hallworthhave said. “She wore what felt right.”

More than 20 years later, a rewind of some of her best looks will serve as definitive proof that Diaz was always a red carpet star. Below, take a look back at 17 of our favorite Diaz moments from 1997 My best friend’s wedding New York City Film Premiere for the 2007 “Poiret: King of Fashion” Costume Institute Benefit at the Metropolitan Museum of Art.