Cameron Diaz's Worst Red Carpet Fashions Before She Was A Star

Cameron Diaz took a massive step back from Hollywood, though she’s resurfaced in recent years as an entrepreneur and philanthropist rather than an actress. Back at the beginning of her career, however, Diaz was more likely to be seen working the red carpet instead of the boardroom, and her fashions at that time were definitely a statement, to say the least. Let’s look back on some of Diaz’s most eye-catching and unflattering red carpet photos from the early stages of her career.

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In 2014, after receiving mixed reviews on her performance in the Annie remake, Cameron Diaz retired from her acting career that spanned 20 years. With all that time on her hands now, she was able to focus more on her personal life, including marrying her now-husband Benji Madden and welcoming her first child, a daughter the happy couple named Raddix.

Latest Photo Of Cameron Diaz

SANTA MONICA, CALIFORNIA – MAY 19: (L-R) Smokey Robinson and Cameron Diaz attend the EEEEEatscon 2019 at Barker Hangar on May 19, 2019 in Santa Monica, California. (Photo by Tommaso Boddi/Getty Images)

Diaz’s acting debut came in 1994 when she starred opposite Jim Carrey in The Mask. Previously, the California-born actress had begun a modeling career while still attending high school, but the comedic film was exactly the boost Diaz needed to make her way to the silver screen. A few years later, in 1997, she was cast in a supporting role in the Julia Roberts romantic comedy My Best Friend’s Wedding.

Still, Diaz wasn’t the household name that she is today until she starred in her raunchiest comedy yet, There’s Something About Mary. The film was released in 1998, which is coincidentally the same year that she broke up with her TSAM co-star and boyfriend Matt Dillon. From there, Diaz went on to star in several blockbuster hits, like Charlie’s Angels, The Holiday, My Sister’s Keeper, and Bad Teacher, to name just a few. Those early years on the red carpet were fascinating to see, as Diaz often made a splash with her appearance, but not always in a good way.

The Age Of The Oversized Scarf

(Featureflash Photo Agency/Shutterstock.com)

In this photo, taken at the 2002 Los Angeles premiere of Gangs Of New York, Diaz wore a pair of red boots, black fishnets, a knee-length pencil skirt, and a long sleeve black t-shirt that reveals just a slice of her midsection. Up top, Diaz accessorized with an oversized white knit scarf that’s nearly as big as she is. The rest of Diaz’s outfit was uninspired but mostly fine. The scarf, however, threw off the entire ensemble and made the utterly gorgeous Diaz look like she had no neck.

A Little Too Much Of Everything

At the 2001 premiere of Vanilla Sky, Diaz certainly drew eyes, but we’re not so sure that was a good thing in this outfit. First of all, she wore a pair of possibly velvet bell-bottoms embroidered with flowers and little specks that unfortunately made the pants look dusty. Her brown and white blouse was tied up in front, which gave fun, wild-child energy to the look, but was an odd choice to pair with the pants. As if her pants and two-toned blouse weren’t loud enough, Diaz capped off the look, literally, with a brown beret of sorts. She also wore a red, plastic bracelet and carried a purple crochet bag.

Remember Dresses Over Jeans? Diaz Does

For a brief, shining moment in history, one of the biggest trends in Hollywood was wearing jeans under a dress. Proving herself to be on-trend, Diaz also tried out the style, wearing a green dress with a swirling gold pattern over a pair of blue jeans. Oddly enough, she chose to wear a pair of purple, closed-toe heels and, since it was the early aughts, a lacy cover-up that she threw around her neck like a scarf.

Why Choose When You Can Wear Both?

Here’s another outfit that’s essentially a two-in-one special. Diaz wore a pair of dark pants beneath a floral print white dress that draped flatteringly across her shoulders. It left plenty of room for Diaz’s necklace, seemingly a piece of decorative rope, to shine. Unfortunately, the droopy fabric also made it seem as if Diaz was playing dress-up with her grandmother’s draperies.

My Fair Juliet

Strangely enough, we think we’ve got Diaz’s Gangs Of New York co-star Leonardo DiCaprio to blame for this next look. After he starred in the 1996 Romeo + Juliet adaptation of the famed Shakespeare play, renaissance fashion made a brief, but impactful, comeback, and it’s clear to see that Diaz wasn’t immune to the trend in 1998. We like the idea of this gaping blouse, but something about the delivery is off. What we will give Diaz is kudos for are the sheer overshirt she wore and those fun and flirty flowing sleeves.

9/17/97 Hollywood, CA. Cameron Diaz and Matt Dillon at the premiere of “In & Out.”

This early red carpet photo of Diaz and her then-boyfriend Matt Dillon is a blast from the past. For this red carpet event, Diaz went low-key in a little black dress with a deep, plunging neckline. Her iconic blonde hair was worn in choppy, short layers that perfectly framed her face. One thing that hasn’t changed from this red carpet photo to more recent ones is that bright, glowing smile that helped launch her career.