Angelina Jolie’s best nineties looks

A symbol of perfection, supernatural beauty, and humanitarian commitment, Angelina Jolie infused a new edgy, punk, and gothic aesthetic, into the pop culture of the 1990s and 2000s. Since 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 Couture.

by Violaine Schütz.

Published on 20 October 2025. Updated on 19 February 2026.

Many people today associate Angelina Jolie with a highly sophisticated image and neutral-toned, glamorous, understated looks. The American 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. Her public speeches addressing her preventive double mastectomy moved audiences worldwide.

Angelina Jolie, star of Couture

The actress also made the headlines as the new face of Guerlain, but also for launching her fashion label Atelier Jolie, and for her directorial debut. On February 18th, she impressed audiences and critics alike with her role in Alice Winocour’s feature Couture, in which she embodies a horror movie director who learns she has breast cancer.

Since her divorce from Brad Pitt, the 50-year-old star has come to embody a certain kind of wisdom, a perfection of mind and body, and a sense of balance. She is often seen surrounded by her children, like a tight-knit tribe.

A former troubled punk teenager turned glamorous movie star

Yet, in the 1990s and early 2000s, Angelina 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 would dress in black, dye her hair raven-black or purple, and go to hardcore punk concerts.

She would self-harm, collect knives, isolate herself in her room, and fight against multiple addictions. Her teenage dream? To become a funeral director. But her beauty eventually caught up with her. Soon, she was modeling and making appearances in music videos. Then came her first 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 interest in BDSM. She would live 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.

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.

A major influence on today’s models

Gradually, the actress established herself as a dangerously beautiful, almost fatal icon. Scandals followed 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 fell in love with the Maleficent actress on the set of Mr. and Mrs. Smith (2005).

From that point on, Angelina Jolie entered a new realm, that of Hollywood royalty. Yet, the rebellious, sexy actress 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 fashion 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 a 1980s rock star. A sexy witch aesthetic that suited an era celebrating the rise of powerful women, who embraced their body and spoke their mind unapologetically…

Coutures (2026) by Alice Winocour, currently in cinemas.