Charlize Theron's 20-Year Oscars Style Evolution

Charlize Theron_Red Carpet_Split - Getty - H 2020
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A longtime face of Dior, the 'Bombshell' nominee is likely to choose an edgy gown, or even a suit, for Sunday's ceremony after wearing Vera Wang to her first Oscars in 2000.

Sunday could become the first time Charlize Theron wears a suit to an Oscars ceremony. She will be attending her 11th Oscars, where she's nominated for leading actress for Bombshell. Theron has donned gowns by Dior to a majority of the ceremonies she's attended over the past 20 years.

She reportedly parlayed an initial $5 million, three-year deal with the French fashion house in 2004 into a partnership lasting more than a decade. So far this season, Theron has worn Dior Haute Couture to the Golden Globes (a partial bustier top with a green silk gown), Givenchy to the SAG Awards (a silver hand-embroidered top and black crepe de chine skirt), Louis Vuitton to the Costume Designers Guild Awards (a gold dress with puffed sleeves and matching sequined headband) and Givenchy to The Hollywood Reporter's Women in Entertainment breakfast (a lavender Resort 2020 suit and black top).

Further showing that a suit isn't totally out of the question for the Oscars this year, Theron donned trousers for the Oscars nominees luncheon, the Long Shot premiere in New York and multiple Bombshell screenings.

Here's a look back at Theron's Oscars ensembles — that went from experimental to classic to edgy — and what viewers can expect from the star and her stylist, Leslie Fremar, on Sunday for the 2020 Academy Awards.


For her first Oscars, Theron showed some skin in a backless orange Vera Wang gown.


She channeled Old Hollywood with her hair in finger waves, keeping her makeup minimal alongside her noticeable tan. While taking home the best actress trophy for Monster, Theron wore an embellished beige Gucci gown. 


The next year, Theron returned in a baby blue strapless, ruffled tulle dress by John Galliano for Christian Dior gown. The brunette walked the carpet hand-in-hand with Stuart Townsend.


Perhaps the biggest departure from her otherwise classic and dreamy looks, Theron's forrest green gown featured an asymmetrical shoulder with an oversize bow. The North Country nominee's dress — again by John Galliano for Dior — was complemented with a retro beehive hairdo. 


Four years later she went with another bold choice. Theron's lavender Dior Haute Couture dress with rosy accents that, as Glamour put it, are "clearly intended to do one thing only — draw your attention towards Charlize's breasts." 


It was a return to classic glam when Theron chose a white Dior peplum gown. Her pixie hair was the predecessor of this season's bowl cut and subsequent short 'do. 


Going minimal, Theron wore what THR called at the time, a "low-key Dior gown that was essentially a sheath." The red carpet dress, with sheer straps and a mermaid silhouette, was accessorized with a stunning 31-carat diamond cluster Harry Winston necklace.


With her hair swept to one side, Theron wore a plunging crimson Dior Haute Couture dress. But the big statement was the Harry Winston Secret Cluster diamond and platinum necklace (totaling 48.8 carats). Along with a ring and earrings, her Harry Winston gems were worth $3.7 million.


The presenter chose a fresh fabric in 2017, sparkling in metallic. And her gold lamé Dior gown wasn't the only thing that shined; her 59.9 carat diamond drop earrings from Chopard's "Garden of Kalahari Collection" stole the show. THR had a behind-the-scenes look at the making of her golden gown. 


In contrast to her blonde waves or pixie cuts of Oscars past, Theron debuted a sleek, "chopped" brunette bob at the Oscars last year. "When I saw the beautiful light Japanese indigo fabric on her Dior dress, I immediately knew I wanted to create a dramatic contrast with her hair," hairstylist Adir Abergel told THR at the time. THR wrote that the transformation helped "end award season on a dramatic note."  

To top if all off, she added to the modernist ensemble with 360 carats of Bulgari diamonds, sapphires and emeralds. Her Serpenti necklace alone showed off nearly 80 carats of diamonds.