Since her debut on the red carpet at the Academy Awards in 1986 at the young age of 10, Angelina Jolie has captivated audiences with her impeccable sense of style. From film premieres to press conferences, Jolie has always made a statement with her fashion choices. Whether it was wearing a vial of her then-husband Billy Bob Thornton’s blood around her neck in 2001 or stunning in a black gown with a thigh-high slit at the Oscars in 2012, Jolie has never shied away from taking risks.

Despite her iconic fashion moments, Jolie maintains that she is not driven by trends. In an interview with Vogue for her September 2023 digital cover, she expressed, “I’m not someone who likes clothes to consume her life. And I don’t love the idea of being ‘influenced.’ But because we live in our clothes, it is so much a part of who we are, and something that’s important to explore, especially for young people.”

While Jolie may prefer elegant neutrals in her everyday wardrobe, she understands the impact of a show-stopping fashion moment. From dazzling in rhinestones at the 2025 Golden Globes in a McQueen creation to embracing Haider Ackermann’s innovative designs in an asymmetrical white dress, Jolie continues to push boundaries with her sartorial choices.

As Angelina Jolie celebrates her 50th birthday, Vogue takes a trip down memory lane to revisit some of her most unforgettable red carpet looks.