On her 50th birthday, Charlize Theron remains not only one of Hollywood's most versatile and admired stars, but also one of its most stylish, always able to take her classic beauty to truly intriguing and chic places. The Oscar-winning actress has graced countless "Best Dressed" lists over the decades, spanning from her breakout in the 1990s to her current effortless "cool girl" aesthetic well into the 2020s.
Her beauty and style have undergone a significant evolution, however, in ways we might not even realize. In honor of her milestone day, Megan Watkins, Head Stylist at online fashion destination SilkFred, broke down Charlize's style shift over the years. "Charlize Theron's style evolution is one of the most compelling in Hollywood," Megan told HELLO!. "She has had an incredible journey from statuesque starlet to fashion risk-taker, underpinned by an unwavering sense of poise and confidence."
During the early days of her career, the actress leaned into some of the more classically feminine styles of the era, betraying her youth as well given she made her film debut in 1995 when she was just 20 years old.
At the Tommy Hilfiger "Rock Style" Exhibit at The Metropolitan Museum of Art, 1999
"In the late '90s and early 2000s, we saw Charlize lean into timeless, feminine glamor – beautiful soft pastel gowns, delicate updos, and classic silhouettes that nodded to Old Hollywood elegance," Megan continued.
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At the 76th Annual Academy Awards with her Oscar for Best Actress, 2004
Winning her Academy Award for Best Actress for her chilling turn in Monster proved to be a major highlight. "Her 2004 Oscars look, where she accepted her award in a glittering Gucci gown with delicate straps, remains a defining moment in Charlize's fashion history."
At the 5th Anniversary of the CFDA/Vogue Fashion Fund, 2008
However, as she became more established as an industry mainstay, the actress and eventual mom-of-two found the room to play around with her aesthetic a bit more, most notably with more gender-neutral edges.
"In the years that followed, particularly through her collaboration with stylist Leslie Fremar, Charlize began to embrace a more minimalist, sculptural, and androgynous aesthetic," Megan noted, citing her 2013 Academy Award appearance as a significant point in that journey.
"It was clean, architectural, and bold, signaling a new era of high-fashion risk-taking that felt super modern and fashion-forward."
At "The Last Face" Premiere during the 69th annual Cannes Film Festival, 2016
"Over the years, she's become known for her razor-sharp tailoring – often favoring Dior suiting and monochrome ensembles that deliver impact through silhouette rather than embellishment," Megan continued.
"Take her 2016 Cannes Film Festival look for example, a classic black tuxedo with an unbuttoned white shirt and diamond necklace. This was the perfect example of how she plays with gender norms while still exuding glamor."
That also became prominent thanks to her growing association with the Dior brand as the face of J'Adore, with her luminescent presence in particular becoming a defining part of the brand's identity, before being replaced by Rihanna in 2024.
"Even her beauty evolution tells a story: from soft curls and golden tones to bold pixie cuts and platinum blonde, Charlize uses fashion and styling to reflect different facets of her persona."
At the Charlize Theron Africa Outreach Project 2024 Block Party, 2024
Megan concluded with: "What sets her apart from many of her contemporaries is her ability to embody power dressing without ever looking severe. There's always a touch of softness or sensuality – whether it's a sheer panel, a plunging neckline, or a barely-there backless gown. She's not trend-led; she's timeless, and that's why her style continues to resonate."
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The Monster star was associated with the Dior brand for two decades, joining as the face of J'Adore in 2004 and making annual appearances at their fashion week shows
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