The Inappropriate Cameron Diaz Outfit That Will Always Haunt Her

Throughout fashion history, there have been many red carpet looks that left a mark on our collective consciousness, though not always in the best way. Take Barbra Streisand's sheer dress at the 1969 Academy Awards, which revealed more skin than the star anticipated. Decades later, there's Pamela Anderson's pink fuzzy hat and corset combo at the 1999 VMAS, which resulted in some raised eyebrows and questions about the event's dress code. Then, there's Cameron Diaz, whose dress at the 2000 Academy Awards still looms large in discussions of her style.

Although one could argue the look was beautiful, at the time, the Versace number, which featured a very deep V-cut neckline, was scandalous for such a formal occasion. In 2025, it could be an example of how to ace the sheer clothing trend. But it wasn't just the cut that was the issue. The sheer black fabric and lace detailing gave sexy, witchy vibes. At a different function, it would have been a fashion success story. But at the Academy Awards, where elegant gowns reign supreme, it looked severely out of place.

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Diaz certainly isn't the first celebrity to miss the mark at such an event. For example, Gwyneth Paltrow has worn several inappropriate red carpet outfits. But, unsuitable or not, Diaz stands by the look. "It's one of my favorites," she told Vogue during an interview in 2025. "It's such a beautiful wisp of a dress." However, she acknowledged that standards for red carpet dressing have shifted toward more formal looks, suggesting that the dress would have been more appropriate in its own era. "There wasn't the whole fashion of it all," she added. 

When it comes to getting dressed in the 2020s, Cameron Diaz has mastered a sleek, sexy style with a fun, sporty edge. There's a bombshell feeling to her outfits but they never fully veer into the boho maximalism that was so popular during the 2000s. "I've never been like a ruffly girl or overly feminine," she told People, admitting she's never been one for following trends. "I just kind of like clean lines."

Those sensibilities have spilled over into Diaz's on screen personas. She revealed to Vogue that she's occasionally pulled items from her own closet to inspire her film wardrobes, including a pair of beloved Chloe pants — "They were pants I used to wear all the time," she shared — that the costume team recreated for "Charlie's Angels." "Cameron was a collaborator," the sisters and stylist team Clare and Nina Hallworth, who styled Diaz during the 2000s, told Vogue. "She was always open to mixing designers. She looked beautiful in clothes and she was a pleasure. Cameron was ahead of everyone. She wore what felt right."