Cameron Diaz Outfits That Were Total Flops

Thanks to more than three decades of being a movie star, Cameron Diaz has long had a place in our hearts. We love everything about her, from her comedic talents to her laid-back, California-girl style. And over the years, she's worn some stunning red-carpet outfits, from the Chanel mini she donned at the 2003 Golden Globes to the white Valentino gown she wore to the event in 2007 (yes, the same Golden Globes gown Cameron Diaz wore for revenge and had everyone staring at). Not one to just follow trends, Diaz has always been gifted at staying true to her own sense of style, whether she's going for a relaxed vibe or glamming it up in a ballgown. 

But nobody gets it right all the time — not even movie stars. There have also been occasions when the "Bad Teacher" actor has sartorially dropped the ball. Many of her biggest outfit flops have to do with her and her stylist failing to read the room, either ending up too casual for a televised red carpet or too sexy for an elegant event. Let's just say that Cameron Diaz's inappropriate dress at the 2000 Oscars had everyone staring. The good news is that every wardrobe blunder Diaz has made should serve as proof that nobody's perfect, and at the end of the day, clothing is an art form that's there to start a conversation. Ultimately, fashion is in the eye of the beholder, but we personally couldn't warm to the following looks from the gorgeous Diaz. 

We're all for risqué dresses when the moment calls for it, but of all the red-carpet events throughout awards season, the Oscars is the worst place to play with that aesthetic. This is an event that demands sophistication — one of the few places you can get away with the ultra-glam gown of your fairy-tale dreams. Sorry, Cameron Diaz, but wearing a sheer black dress that shows your underwear and isn't even buttoned up all the way to the Oscars is just outrageous.

Yes, the '90s was a different time, and the dress-over-pants trend was not only accepted but also popular. Still, we can't look back at this look from the 1999 Golden Globes and call it anything but terrible. It's not just the dress-over-pants thing, but the thick, baggy material and fit of the dress paired with thick and baggy pants creating an odd silhouette. To add insult to injury, the closed shoes create a bulkier effect still, and we won't even start on the cord-tassel necklace.

It's been more than two decades since Cameron Diaz wore her blush-colored and floral-designed satin Emanuel Ungaro getup to the 2002 Academy Awards, and we're still confused. There's just too much going on, from the large red flowers that blend in with the carpet to the single pleating section of the skirt and the plunging wrap neckline. The embellished belt worn at an angle is also a mess. Throw in the pop of turquoise on Diaz's wrist and the purple-and-blue trim of the top, and we're beyond lost.

There's a silver lining to Cameron Diaz's summery look at the 2004 "Shrek 2" premiere: Even A-listers suffer from common wardrobe mishaps, like creasing disasters. These days, stars often travel to the red carpet in vehicles large enough for them to stand in so they don't have this problem; after all, obvious wrinkles can completely ruin a look. Without the fold lines in her satin skirt, Diaz probably would have won our approval here for a look that was quintessentially Y2K, from the metallic banana bag to the jewel-studded flip-flops.

Is there anything inherently wrong with the jeans and tank top Cameron Diaz wore to the Nickelodeon Kids' Choice Awards in 2005? No. It would've been fine for a trip to the mall or lunch by the beach. But to a televised red-carpet event where most of the guests are in formal wear, even if it has a fun vibe? Absolutely not! The knit indigo scarf tied to her bag may have been intended as a fashion statement, but it's just pushing this look further into the "mall" pile.

While Cameron Diaz's usual crime on the red carpet is under-dressing, she took that literally at the 2002 Cannes Film Festival. The "There's Something About Mary" star once again gave up the opportunity to wear a glamorous frock, opting for a see-through mesh number that showed her underwear, even if it was by Versace. In 2025, the prestigious event put a ban on naked looks, so this sultry dress wouldn't fly today, but back in 2002, this inappropriate Cameron Diaz outfit had everyone at the Cannes Film Festival staring.

This one hurts because the all-black look Cameron Diaz wore to the "Back in Action" German premiere in January 2025 was so close to being a hit. Monochromatic black with on-trend wide-leg slacks, pops of sheer material for balance, and a power coat? The ingredients were there. But we can't get around the excessive length of the coat, which trailed on the floor. This maybe could have been saved by a pair of sleek heels, but the chunky flats enhanced the illusion that Diaz was swimming in material.

We know Cameron Diaz is more than capable of a killer red-carpet look, but for the 2014 premiere of "Annie," the A-lister ended up looking overly frumpy and had us all yawning. The A-line dress itself was okay, but the heavy gray color paired with opaque black tights and mid-calf boots made this ensemble seem much more like an office holiday party 'fit rather than something you'd wear to a New York City movie premiere. It wasn't horrible, but it also wasn't a fashion win.

Speaking of office-ready looks, Cameron Diaz really embraced the corporate-wear trend at the 2012 film premiere of "What to Expect When You're Expecting." Aside from the lower V-neck of her white blouse, this entire look could have been copy-pasted from the average working woman's wardrobe. Perhaps strappy sandals and a lighter fabric on the pants could have made this outfit not merely corporate-coded, but in reality, it was just corporate. There's a way to put your own creative spin on corporate wear, but this wasn't it.

Sometimes, fashion risks pay off, and other times, they haunt you. At the 2009 MTV Movie Awards, an event reserved for fun red-carpet attire, Cameron Diaz rocked skinny jeans (which, to her credit, were trending at the time), a military-jacket-style top with neon animal print, and bright-blue suede boots. She does get brownie points for creativity, but especially at an awards show, this casual look didn't land the way it could have. No one's shoes should be that distracting!