Angelina Jolie has been turning heads on the red carpet since she was just 10 years old. Her debut at the Academy Awards in 1986 featured a lacy, unmistakably ’80s ensemble – the first of many unforgettable fashion moments that would cement her as one of Hollywood’s most stylish stars.

Over the past four decades, Jolie’s fashion evolution has been anything but predictable. From her edgy early 2000s phase – complete with a vial of then-husband Billy Bob Thornton’s blood – to her 2012 Oscars appearance in a now-iconic black Versace gown with a dramatic thigh-high slit, she’s never played it safe. Whether she’s in a slinky slip dress, a vintage-inspired gown, or channeling gothic elegance à la Maleficent, Jolie owns every look with unapologetic confidence.

In the late ’90s and early 2000s, she frequently wore designs by Versace, Marc Bouwer, and Randolph Duke. More recently, she’s embraced a refined, minimalist aesthetic, gravitating toward labels like Brunello Cucinelli while occasionally returning to her roots with classic Versace. “I don’t change things often,” she told British Vogue in her March 2021 cover story. “Enjoying your vintage pieces… and rediscovering some vintage shops seems like part of the way forward.”

In 2023, Jolie took her passion for fashion to the next level by launching her own brand, Atelier Jolie. The label is all about collaboration, sustainability, and creativity. “It stems from my appreciation and deep respect for the many tailors and makers I’ve worked with over the years,” she shared on Instagram, highlighting her commitment to using vintage and deadstock materials.

Now, as she celebrates her 50th birthday, we’re looking back at 25 of Angelina Jolie’s most striking style moments—from her early days in lace to her most polished, modern-day ensembles. One thing’s for sure: she’s always been a fashion force to be reckoned with.