A Nostalgic Look Back At Cameron Diaz’s Style Evolution

marie claire revisits the actress' most iconic fashion moments

Our forever style muse and girl crush might have taken a step back from the spotlight, but actress Cameron Diaz has no shortage of memorable red carpet appearances and iconic on-screen moments. From her early days as America’s sweetheart in My Best Friends’ Wedding to the Charlie’s Angels 2 premiere with Drew Barrymore and that bottle of Dom Pérignon, marie claire looks back at the star’s style evolution.

1994 Baby-Faced At the Video Software Dealers Association Convention 

Cameron Diaz
(Credit: Getty Images)

On July 28, 1994, Diaz made her film debut with The Mask. Just three days before the film’s release, the then-21-year-old was an epitome of 90s style and charm, wearing a black tee and ice-blue silk mini skirt, at the 13th Annual Video Software Dealers Association Convention.

1997 At My Best Friend’s Wedding New York City Premiere Party

Cameron Diaz and Julia Roberts
(Credit: Kevin Mazur Archive/WireImage)

In 1997, Diaz starred in My Best Friend’s Wedding, smiling here in a timeless black bodycon dress alongside Julia Roberts at the premiere of the rom com classic.

1998 In There’s Something About Mary

Cameron Diaz There's Something About Mary

Diaz’s lead role in the 1998 comedy film There’s Something About Mary made her a household name and taught us all a lesson in trans-seasonal dressing with this sweet lavender cardigan. Not only did the film take home four  MTV Movie Awards, Diaz won the New York Film Critics Circle Award for Best Actress, MTV Movie Award for Best Performance, American Comedy Award for Best Actress, and Blockbuster Entertainment Award for Best Actress.

2000 At the Charlie’s Angels Premiere

2000 Charlie's Angels Premiere
(Credit: Chris Weeks/Liaison)

On October 22, 2000, Cameron Diaz, in a thigh-grazing little black dress, fishnets and leather boots, was hand in hand with Drew Barrymore and Lucy Liu celebrating the Charlie’s Angels premiere in Los Angeles. Name a more iconic female trio!

2000 Dancing in Charlie’s Angels

Cameron Diax Charlie's Angels

And of course, there’s this mood-boosting Charlie’s Angels scene. Who said you need a party dress, diamonds and stilettos to have a good time?

2002 On the 74th Annual Academy Awards Red Carpet

74th Annual Academy Awards
(Credit: Frank Micelotta/ImageDirect)

Diaz donned a kimono-inspired Emanuel Ungaro Couture gown, and completed her look with a Fred Leighton necklace worn around her waist, later picking this look as one of her favourite red carpet appearances.

2003 Cheersing En Route to The Charlie’s Angels 2: Full Throttle Premiere 

Cameron Diaz and Drew Barrymore

Walking themselves to the the Charlie’s Angels 2 premiere after their party bus broke down, Cameron Diaz and friend Drew Barrymore showed their wild and carefree sides before getting ready for the red carpet.

2003 At the Charlie’s Angels 2: Full Throttle Premiere

2003 Charlie's Angels Premiere
(Credit: Kevin Winter/Getty Images)

At the Charlie’s Angels sequel’s premiere in 2003, the trio dressed in coordinated white outfits. After a shoe mishap on the day, Diaz abandoned her heels, walked the red carpet barefoot and still towered over her co-stars.

2007 On the Shrek the Third UK Premiere Green Carpet

Shrek 3 premiere
(Credit: Getty Images)

Voicing Princess Fiona in all four Shrek movies didn’t interrupt Cameron Diaz’s chic-as-ever style, wearing Chanel next to her on-screen husband at the UK premiere.

2007 At the 79th Annual Academy Awards

2007 Academy Awards
(Credit: Chris Polk/FilmMagic)

Diaz’s white off-the-shoulder Valentino dress, coupled with Cartier Jewellery, left an impact when she presented the 79th Annual Academy Award for Best Animated Feature Film.

2008 On the 80th Annual Academy Awards Red Carpet

2008 Academy Awards
(Credit: Dan MacMedan/WireImage)

Keeping to a similar theme a year later, Diaz wore an ballerina-pink Christian Dior dress with her signature golden blonde hair swept into a face-framing ponytail.

2010 At the 67th Annual Golden Globe Awards

2010 Golden Globes
(Credit: Getty Images)

Diaz stunned in a fiery red satin Alexander McQueen gown at the 67th Golden Globe Awards – even the downpour couldn’t undermine her confidence and glamour as she walked the red carpet. 

2010 Presenting At the 82nd Annual Academy Awards

2010 Academy Awards
(Credit: Getty Images)

Later that year, Diaz presented with Steve Carell at the Academy Awards, taking a more angelic approach in a champagne Oscar de la Renta gown with sparkling gold paillette embroidery.

2012 At the What To Expect When You’re Expecting Los Angeles Premiere

2012 movie premiere
(Credit: Getty Images)

Pictured here with co-star Elizabeth Banks, Diaz wore a black Valentino mini-dress to the Los Angeles premiere of What to Expect When You’re Expecting, switching her go-to beach waves for a brighter, textured bob.

2014 At The Other Woman Premiere

The Other Woman LA premiere
(Credit: Getty Images)

Diaz looked the part with her gravity-defying and daringly low-cut Stella McCartney minidress and gold-studded Manolos at the LA premiere of The Other Woman.

2016 At Her Book Signing in California

2016 Book Signing
(Credit: Getty Images)

Although Diaz left showbiz in 2014, she shared her wellness secrets with fans in her book, The Longevity Book. Autographing copies at a Huntington Beach Barnes & Noble, the actress wore a classic blazer, tee and jeans combination with an eye-catching red lip. 

2016 At A House of Harlow 1960 x REVOLVE Party

Cameron Diaz and Benji Madden

At a Los Angeles party in 2016, Diaz was spotted embracing her husband, Good Charlotte guitarist Benji Madden, wearing a white power suit. The pair married a year earlier in 2015, and welcomed their first child, Raddix Madden, on December 30, 2019.

2019 At Lucy Liu’s Hollywood Walk of Fame Ceremony

Charlie's angels reunion
(Credit: Getty Images)

Following her departure from Hollywood, Cameron Diaz kept it casual with understated neutrals and denim to reunite with Drew Barrymore and Lucy Liu at Liu’s Hollywood Walk of Fame ceremony in 2019.

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