Cameron Diaz's Inappropriate Outfit At The 2000 Oscars Had Everyone Staring

The Oscars marks one of Hollywood's biggest nights, as A-list actors and filmmakers gather to celebrate the best movies of the year. Of course, before they hit the stage to accept their awards, celebrities dazzle in gorgeous outfits on the red carpet, but everyone's looks don't always fit folks' definition of "appropriate." Here's a cautionary tale: At the turn of the century, "The Mask" actor Cameron Diaz became the it-girl of the moment with her blond hair and winning smile. Her chic fashions were revered, as they showed off her figure, but for the Oscars in 2000, Diaz went too bold and ended up wearing an ensemble that was down-right inappropriate. 

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Diaz walked the carpet in a custom black lace dress by Versace. The body-hugging outfit included a super-deep plunging neckline with a button-down feature on the bodice. The gown was floor-length, but a high slit showed off Diaz's long legs. The nearly see-through material revealed a black panty underneath and proved why exposed underwear was just as risky then as it was in 2023 when it returned to the fashion fore. Diaz wore the gown all night, later attending the Vanity Fair Oscars after-party in the sexy black number as well. She completed the outfit with classic black peep-toe heels and a matching clutch purse. 

Sadly, Diaz's attempts to make the outfit look elegant fell flat and made the "Charlie's Angels" actor stand out for dressing too casually. In a sea of celebrities that were dressed to the nines on Oscars night, Diaz and her lack of fabric unfortunately looked tacky. 

If Cameron Diaz was looking to garner attention with her dress choice at the 2000 Oscars, she certainly got it — but for the wrong reasons. Her peek-a-boo dress showed off her body in a way that was both boring and a tad tasteless. She would have been better off learning how to wear a high-slit dress without baring it all so the outfit felt balanced. Instead, the sheer black lace made the garment feel more like a nightgown than formalwear. It had the appearance of a lace cover-up, which gave the impression that Diaz didn't take the event seriously.  

Diaz's platinum-blond bob washed out her face, making her look even paler in the black ensemble. This was a clear example of the problematic "heroine chic" Y2K trend that glamorized unrealistically thin appearances accompanied by pale skin and heavy eyes. There were also elements of the witchcore fashion aesthetic that we love in the fall, which felt out of place at a Hollywood event that typically favors bold glamour — and occurs in March each year. Some colorful eyeshadow would've helped this look by pairing nicely with her red pedicure.

Speaking with Vogue in January 2025, Diaz admitted that she has no regrets about walking the Oscars carpet in this ensemble. In fact, she said the outfit is "one of my favorites." Her final take? "The red carpet used to be a lot more relaxed."

Cameron Diaz's 2000 Oscars dress is definitely one of her most inappropriate looks, but her 2002 ensemble isn't much better. The "Bad Teacher" star showed up at the Oscars in a floral Emanuel Ungaro kimono-style gown that was styled as if she'd just gotten out of bed and rushed out the door. The wrap dress featured long bell sleeves, with one side of the skirt in pleats. The ill-fitting garb bunched at Diaz's waist in an unflattering way, which was further highlighted by a strange necklace that she decided to wear as a belt. Her turquoise bracelet clashed horrendously with the red and pink colors of the dress, and her messy updo only added to the unkempt look.

We knew something had to be up here, and as it turns out, Diaz didn't have much time to spend on her 2002 Oscars outfit. Diaz told longtime makeup artist Gucci Westman in a 2020 episode of the latter's "Makeup & Friends" YouTube series that she'd forgotten about the awards show. Westman had stepped in and used her contacts to borrow the Ungaro gown, and although she did Diaz's makeup, she sadly couldn't save the actor's disheveled 'do. "The red carpet is so different now. For my premieres, I would just go to Barney's and buy clothes," the mom of two lamented. Diaz has largely been out of the limelight for years now, save for a few sporadic acting credits, but we hope to see her style evolve when she begins hitting red carpets regularly again.