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.

Publié le 26 april 2025. Modifié le 28 April 2025.

Today, most people think of Angelina Jolie as a highly sophisticated figure, known for her glamorous yet pared-down, neutral-toned looks. After stepping away from acting for a while, the star will return in Maria, a biopic about Maria Callas set for release in February 2025. In recent years, she has made headlines more for her humanitarian work, serving as a UN goodwill ambassador and advocating for refugees, than for her film roles. She has also launched her fashion label, Atelier Jolie, and directed several films.

Since her divorce from Brad Pitt, the now 49-year-old actress has come to embody wisdom, balance, and a kind of perfect serenity, often seen surrounded by her close-knit brood of children.

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.

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 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 instead married Billy Bob Thornton (Landman) in 2000. She 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, Jolie established herself as a dangerously beautiful, almost fatal icon. She was known for sparking on-screen chemistry that often carried over off-screen. In 2005, the media labeled her a “homewrecker” for allegedly causing the split between Brad Pitt and Jennifer Aniston, America’s sweetheart, thanks to Friends. Pitt famously fell for Jolie during the filming of 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 ’90s, Angelina Jolie oscillated between looking like Marilyn Monroe and Morticia Addams. Satin slip dresses, velvet capes, leather jackets and pants, studded belts, black tank tops, vintage evening gowns, boots, tattoos, raven-black hair, pale complexion, and heavily lined eyes—she invented a style later dubbed “succubus chic.” It’s a perfect blend of Old Hollywood glam and vampy ‘80s rock star allure. A sexy, witchy aesthetic that perfectly embodied the rise of powerful women owning their bodies and voices, unapologetically.