Cameron Diaz’s Best Red Carpet Looks Ever: Every Time She Wins Best Dressed

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

While leaving the Berlin screening of his new Netflix film Back to Actionshe turned heads in a full Gucci look with a slicked-back twist that matched her eternally cool California girl look. She ditched the high heels in favor of a pair of Gucci penny shorts that accented her dark denim mom jeans and a sheer blouse, then threw on an oversized coat for an extra layer of swagger.

But former model Diaz, 51, has always been a standout on the red carpet, and her celebrity peers have long praised her edgy, poetic bohemia style that always sets her apart.

To him Vogue May 2003 cover story, by Diaz Charlie’s Angels the costar Lucy Liu she said of her friend’s wardrobe: “For Cameron, it’s an art form, and it’s all about change and change — like changing a skirt into a tube top. Something can cost $10 or $10,000 – either way, if he’s comfortable with it. You make it work. He defines his fashion, and people follow it.”

During her incredible rise in Hollywood, her beauty on the red carpet read like a master class in the minimalism of the ’90s era. She was a fan of all-black outfits that highlighted her mile-long legs and added a kicking red heel to simple black pants with a halter top and a cardigan draped over her shoulders. She loved a jaunty hat, a cropped croptop and lots (and lots) of blue eyeshadow – a look that would feel right at home on today’s Gen-Z style stars.

As she landed bigger roles, she occasionally made the worst-dressed list. At the 2002 Academy Awards she wore a kimono dress by Emanuel Ungaro Haute Couture that is now considered ahead of its time.

“Cameron was a collaborator. He was always open to mixing designers. She looked beautiful in clothes and happy. Cameron was ahead of everyone,” his writers at the time, Clare again Nina Hallworththey said. “He was wearing what he felt was right.”

More than 20 years later, a throwback to one of her best looks will serve as definitive proof that Diaz was always a red carpet winner. Below, check out 17 of our favorite Diaz moments, dating back to 1997 My Best Friend’s Wedding The New York City film premiered at the 2007 “Poiret: King of Fashion” Costume Institute Benefit at the Metropolitan Museum of Art.