Cameron Diaz Took A Major Style Gamble At The Cannes Film Festival In 2002

Cameron Diaz made some bold fashion choices in the early 2000s, and one of her most risque looks was the dress she walked the red carpet in at the Cannes Film Festival in May 2002. She was there to support her Martin Scorsese-directed film, "Gangs of New York." For the occasion, Diaz flaunted her figure in a sparkling Versace gown that clung to her frame. 

The piece was netted with a single shoulder strap. It was a bold, sheer look with sequins that shimmered as the cameras flashed to catch her photo. She wore black lingerie-style shorts underneath, and the "Charlie's Angels" actor flashed plenty of leg in a full-length skirt with a high slit, which was knotted at the top of her thigh. Her bright blond hair and fair skin made the black gown stand out even more. To complete the Cannes look, Diaz added open-toe black heels and kept the accessories minimal with thin silver bracelets.

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At a glance, one could mistake Diaz's gown for being see-through, and it's quite possible that the revealing number played a part in the Cannes Festival implementing new dress code rules in later years. Initially, "The Sweetest Thing" actor received blowback for the dazzling faux-nude gown. In May 2013, the piece made the sartorial dishonor roll when Entertainment Weekly deemed it one of the all-time worst Cannes outfits. Perhaps one of the reasons Diaz decided to leave the spotlight behind was because of the unfair scrutiny she was subjected to with her fashion-forward looks. But while her alluring Cannes dress offended the fashion sensibilities of some, it eventually earned praise in later years, nabbing a spot on Harper's Bazaar's most glamorous Cannes looks list in May 2020. That wasn't Diaz's only red carpet look that was given a sartorial reappraisal.

Only a couple of months before Cameron Diaz left mouths agape at Cannes, "The Mask" star had fashion experts shaking their heads. She appeared at the 2002 Academy Awards in a kimono-style gown from Emanuel Ungaro that featured red floral designs throughout. Besides a plunging neckline, the piece was fairly modest; it included three-quarter-length sleeves and was loosely wrapped around her figure. Initially, many in the industry had difficulty processing the flowing, flowery gown that was ahead of its time. The dress was maligned and even made Entertainment Weekly's list of all-time worst Oscar looks in February 2009. Eventually, the "Vanilla Sky" actor's floral piece earned her flowers from the fashion community, as Diaz's Oscars moment aged like fine wine. 

A decade later, Diaz sported a bold look at the 2013 Met Gala: a cobalt blue cape dress from Stella McCartney. The cape top had a high neckline and cascaded down her sides, but was cut in a way to leave her midsection exposed. It was a backless number that included a body-hugging skirt. That year's theme was Punk: Chaos to Couture, and the "Bad Teacher" star's ensemble embraced the motif by including a dangerously sharp-looking metallic silver belt. "I feel so chic," Diaz said at the time, per CBS News. 

As evidenced by the above examples, Diaz has taken multiple style gambles over the years, but they may not have all been on purpose. Speaking to Harper's Bazaar in 2010, she mentioned how difficult it could be to make an impact on the red carpet. "I'm so confused at this moment. I don't understand fashion at all right now," Diaz told the publication after saying the stars grab their looks from "the same places."