See a Young Angelina Jolie, Captured in 20 Photos of the Actor Early on

Angelina Jolie’s star power could light a rural town for a calendar year. Since her days as a punk starlet, Jolie has approached her style with unabashed realness, even as the tabloids bristled at her more controversial actions. Some of her fashion moments are referenced today, including by her children. Two years ago, the internet couldn’t help but compare Shiloh Jolie’s pink buzzcut to her mother’s own shaved head back in the late ‘90s. And Zahara Jolie turned heads at the Maria premiere when she wore a silk white dress similar to the Marc Bouwer gown Jolie wore to the 2004 Academy Awards. 

Now, a mother of six, the actress’s rebellious era seems like a lifetime ago. At the turn of the millennium, the public’s perception of Jolie oscillated between goodwill, revulsion, and shock as she had a brief relationship with Billy Bob Thornton and (gasp!) kissed her brother on the lips at the Academy Awards. Still, her singular talent and striking beauty secured her status as a Hollywood icon.

The launch of Jolie’s creative space Atelier Jolie in New York City is a full circle moment in a career that has been marked with iconic style moments and philanthropic work. In an interview with Vogue, Jolie said of the business venture, “I don’t want to be a big fashion designer. I want to build a house for other people to become that.”

Take a trip down memory lane and click through the gallery to see 20 of Angelina Jolie's young pictures, including some of her most iconic early looks.