Cameron Diaz’s Best Red Carpet Looks: All the Times She Won Best Dressed
Don’t call it a comeback, but Cameron Diaz officially returned to the red carpet by making her first appearance on the crimson carpet on Wednesday, January 15, after a decade-long hiatus from Hollywood.
When she stepped out for the Berlin premiere of her new Netflix movie Back in actionshe turned heads in a full Gucci look with a decidedly relaxed twist that matched her eternally cool California girl aesthetic. She ditched the towering heels in favor of Gucci penny loafers, teamed with dark denim jeans and a sheer blouse, then layered an oversized coat on top for an extra layer of swagger.
But former model Diaz, 51, has always walked the red carpet, and her celebrity peers have long praised her directional style, a unique brand of poetic bohemia that consistently sets her apart.
In it Fashion Cover May 2003, Diaz Charlie’s Angels Castor Lucy Liu said of her friend’s wardrobe: “For Cameron, it’s an art form and it’s all about transformation and change — like turning a skirt into a top. Something can cost $10 or $10,000—whatever is convenient for her. She makes it work. She defines her own fashion, and people follow her.”
During her meteoric rise in Hollywood, her red carpet aesthetic was like a masterclass in ’90s-era minimalism. She was a fan of all-black little black dresses that highlighted her mile-long legs, and she added bright red heels to simple black pants with a crop top and a cardigan draped over her shoulders. She sported a chic hat, a revealing crop top, and lots (and lots) of blue eyeshadow—looks that would look right at home on today’s Gen-Z stars.
When she landed big roles, she occasionally made worst-dressed lists. 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 her clothes and was a pleasure. Cameron was ahead of the curve,” her stylists at the time, Claire and I have Holworththey said. “She wore what she thought was appropriate.”
More than 20 years later, a rewind of some of her best looks is definitive proof that Diaz has always been a red carpet winner. Take a look back at 17 of our favorite Diaz moments from 1997 below My best friend’s wedding The 2007 New York premiere of Poiret: King of Fashion at the Metropolitan Museum of Art’s Costume Institute.