One Of Cameron Diaz's Supposedly Worst Fashion Moments Aged Like Fine Wine

When Cameron Diaz showed up to the 2002 Academy Awards, her outfit was labeled as a misfire by fashion experts, but over the years, many have realized that she was likely just ahead of her time. The "Charlie's Angels" star arrived on the Oscars red carpet in a cream-colored kimono-style gown from Emanuel Ungaro. Diaz's wrap dress featured a red floral pattern, plunging neckline, bell sleeves, and a full-length pleated skirt. To cinch the loose-fitting piece to her frame, Diaz added a belt around her midsection, and in typical Y2K fashion, she accessorized with a turquoise bracelet on one wrist. Adding to the carefree look, Diaz's hair was tied up in a loose bun. 

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Originally, the look was not well-received. Diaz's ensemble earned her a spot on the all-time worst-dressed celebs at the Oscars list put together by Entertainment Weekly in February 2009. At the time, the outlet bashed the "Bad Teacher" star's belt and slapdash hairstyle. Over time, opinions on the kimono-style look changed. Years later, the 2002 Oscars dress got its flowers from fashionistas. In March 2023, online fashion influencer Liana Satenstein made an Instagram post reappraising Diaz's flowery outfit. Followers popped up in the comments and heaped praise on the effortlessly chic red carpet appearance.

Part of the initial blowback for the look came from Diaz looking as if she had put in minimal effort. During a YouTube segment with her friend and well-known makeup artist, Gucci Westman, Diaz revealed that her preparation for the 2002 Oscars truly was last-minute. "I'm literally like, 'Oh s***, I'm going to the Oscars, I forgot,'" Diaz said. Speaking about that once-misunderstood outfit gave insight into why Diaz decided to leave the spotlight.

While discussing her 2002 Academy Awards ensemble with Gucci Westman, Cameron Diaz mentioned how her approach to high-profile events had changed. "Red carpet is so different now. For my premieres, I would just go to Barneys and buy clothes," she told Westman in the YouTube video posted in April 2020. The "Back in Action" actor laid out why the red carpet landscape had changed for not only herself, but all of Hollywood. "It wasn't like a whole production where you got judged, or rated, or scored for how you looked," Diaz reminisced.

It may have been a simpler time, but grabbing her own outfits off the rack unfortunately led to some fashion flops. Diaz had one of the worst outfits in Golden Globes history in September 1999. The look (pictured above) could be described as a prototype for the Emanuel Ungaro gown she wore at the 2002 Oscars, as Diaz sported a different kimono-inspired dress. The Golden Globes garment was cream with multi-colored floral designs and and an off-the-shoulder neckline. Diaz had the sleeves of that piece rolled up as she plunged her hands into its deep pockets. Rather inexplicably, the "Vanilla Sky" actor chose to pair the dress with black slacks and black heels.

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Five years later, Diaz was still experimenting with pairing neutral-colored pieces with multi-colored garments. At a premiere for "Shrek 2" in May 2004, she wore a beige bustier halter top with thin spaghetti straps. The outfit screamed Y2K as she coupled it with a satin multi-colored skirt featuring a turquoise waistband. To bring the 2000s red carpet look together, she accessorized with a metallic gold crossbody bag and a pair of large hoop earrings.