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Angelina Jolie’s best nineties looks
A symbol of perfection, otherworldly beauty, and humanitarian commitment, Angelina Jolie infused pop culture in the 1990s and 2000s with a new aesthetic, one that was edgier, punk, and gothic. As her attitude and outfits from that era continue to inspire models like Amelia Gray and Gabbriette, here’s a look back at the actress’s most stunning vintage looks, just as she returns to the screen in Maria.
by Violaine Schütz.
Many people today associate Angelina Jolie with a highly sophisticated image and neutral, glamorous, pared-down looks. The star stepped away from the big screen before returning with Maria, a biopic on Maria Callas released in February 2025. In recent years, the actress has been best known for her humanitarian work as a UN goodwill ambassador advocating for refugees. She also made the headlines as the face of Guerlain, for launching her fashion label Atelier Jolie, and for her directorial debuts. The latter will also appear in Stitches, a feature film by Alice Winocour, coming out on February 18th, 2026.
Since her divorce from Brad Pitt, the 50-year-old star has come to embody a certain wisdom, a kind of perfection of mind and body, and a sense of balance. She is often seen surrounded by her children, like a tight-knit tribe.
Angelina Jolie at the premiere of Gone in 60 Seconds in 2000. Photo by Rune Hellestad/CORBIS/Corbis via Getty Images.
A Punk teen before becoming a glamorous icon
Yet, in the 1990s and early 2000s, Jolie, daughter of actor Jon Voight (Midnight Cowboy), was something entirely different in Hollywood. “Deep down, I’m still and always will be just a punk kid with tattoos,” she once said. As a teenager, she embraced a gothic look: dressing in black, dyeing her hair raven-black or purple, and frequenting hardcore punk concerts.
She practiced self-harm, collected knives, isolated herself in her room, and battled multiple addictions. Her teenage dream? To become a funeral director. But her beauty eventually opened other doors. Soon, she was modeling and appearing in music videos. Then came roles in Hackers (1995), Gia (1998), Girl, Interrupted (1999), The Bone Collector (1999), Gone in 60 Seconds (2000), and, of course, the blockbuster Lara Croft: Tomb Raider (2001), which catapulted her to stardom.
Angelina Jolie at the premiere of Girl, Interrupted in Los Angeles in 1999. Photo by Jim Smeal/Ron Galella Collection via Getty Images.
Rock’n’Roll romances
At the start of her career, Jolie, who would go on to win three Golden Globes and an Oscar, eschewed traditional PR management and followed her own path. In the 1990s, she spoke openly about her bisexuality and her interest in BDSM, living her rock’n’roll love stories in the public eye.
She married actor
She married actor Jonny Lee Miller (Trainspotting), whom she met on the set of Hackers, wearing black leather pants and a white shirt bearing his name written in her own blood. She also famously kissed her brother on the lips at the 2000 Oscars.
(Trainspotting), whom she met on the set of Hackers, wearing black leather pants and a white shirt bearing his name written in her own blood. She also famously kissed her brother on the lips at the 2000 Oscars.
Courted by Mick Jagger, David Duchovny, and Colin Farrell, she eventually married Billy Bob Thornton (Landman) in 2000. Angelina Jolie wore a vial of his blood around her neck during their relationship.
Angelina Jolie’s style in the 90s and 2000s and it’s lasting influence on today’s models
Gradually, the actress established herself as a dangerously beautiful, almost fatal icon. Scandal follows in her wake, and she became known for making her on-screen partners fall under her spell. In 2005, the media branded her a “homewrecker,” claiming she was behind the divorce of Brad Pitt and Jennifer Aniston, America’s sweetheart since the show Friends. Indeed, Brad Pitt had fallen in love with the Maleficent actress while filming Mr. and Mrs. Smith (2005).
From that point on, Jolie entered a new realm: Hollywood royalty. Yet, the rebellious, sexy Jolie of the pre-Brad Pitt years, the one who once pulled a journalist into a swimming pool during a filmed interview, still lingers. Her red carpet looks from that era have notably influenced style icons like Kylie Jenner, Alexa Demie, Gabbriette, and Amelia Gray in recent years.
The pioneer of “succubus chic”
In the 1990s, Angelina Jolie looked like Marilyn Monroe at times, or like Morticia Addams. Satin slip dress, velvet cape, leather jacket and trousers, studded belt, black tank top, vintage evening gown, boots, tattoos, raven-black mane, pale complexion and eyes rimmed in black… Angelina Jolie created an aesthetic that would later be known as “succubus chic.”
It was a perfect blend of Old Hollywood glamour and the vampire-like vibe of an 1980s rock star. A sexy witch aesthetic that suited an era celebrating the rise of powerful women, who embraced their bodies and spoke their mind unapologetically…
Maleficent: Mistress of Evil (2019) by Joachim Rønning is airing on W9 on October 20th, 2025.
Angelina Jolie’s best nineties and Y2K looks
Angelina Jolie at the premiere of Lara Croft: Tomb Raider in 2001. Photo by Jim Smeal/Ron Galella Collection via Getty Images.
Angelina Jolie at the London premiere of Mission: Impossible 2 in 2000. Photo by Antony Jones/UK Press via Getty Images.
Angelina Jolie and Billy Bob Thornton at the Gone in 60 Seconds screening in Los Angeles in 2000. Photo by S. Granitz/WireImage via Getty Images.
