A-list actresses like Angelina Jolie only come around once in a generation. Since making her Hollywood breakthrough with Girl, Interrupted in 2000, Angie has become not only a bonafide movie star but an international icon. As her career — and personal life — has shifted track across three decades, so has the actress’ sartorial inclinations. From Hackers-era cyber attire and Lara Croft biker chic to Hollywood mom glam and Brangelina ballgowns, Angie has gone from 90s goth to 00s glam and beyond. “I am still at heart — and always will be — just a punk kid with tattoos,” Angie told Vogue of her fashion choices in 2004. Does the sound bite still hold true in 2021? Here, to celebrate the star’s 46th birthday and new movie Those Who Wish Me Dead, we chart Angelina’s style evolution across three decades.

jon voigt with his arm around angelina jolie on the red carpet

At the reopening of Tru, 1991

The daughter of actors Jon Voigt and Marcheline Bertrand, Angelina made her film debut at age 7, playing opposite her father in a bit role in 1982’s Lookin to Get Out. A few years after her first screen appearance, however, Angie dropped out of acting classes to pursue a career as a funeral director, enrolling in at-home embalming courses. In 1991, at age 16, Jolie restarted her theatre studies, and, two years later, began her acting career with a starring role in low-budget sci-fi flick Cyborg 2. Angie’s early career style — seen in headshots, photo sessions and at premieres — took in the 90s most ubiquitous trends, all lightly tinged with the actress’ goth-y inclinations. Think babydoll dresses in bruise purple, bustiers in blood crimson and black-as-night leather. Here, with her father — and first co-star — Angie wears the era’s oversized suiting with matching camisole and two swipes of eyeshadow in the same shade of corpse gray.

angelina jolie with a buzz cut on the red carpet with david duchovny

At the premiere of Playing God, 1997

In 1995, Angie garnered her first mainstream film role, starring as cybercriminal Kate Libby in teen crime film Hackers. As Angie established herself in the industry, she came into herself sartorially, fully embracing her gothic predilections. Throughout the mid-90s, the actress wore velvet capes, iridescent slip dresses and velour maxi dresses. Here, at the premiere of Playing God, Angie wears a floor-length leather coat — and a buzzed head — perhaps inspired, in part, by the cyber-goth style of her Hackers character.

angelina jolie smiling on the red carpet wearing a slit dress

At the Emmy Awards, 1998

The aforementioned buzzcut, which Angie rocked throughout 1997, actually came courtesy of her turn as ill-fated supermodel Gia Carangi in the eponymous HBO miniseries. For the role, Angie was nominated for (and won) myriad of the television industry’s most prestigious awards from a Golden Globe to a SAG statuette. For the Gia awards show circuit, the actress abandoned her goth-y get-ups for softer, more glamorous garb. Think gowns in silver sequins, intricate beaded embroideries and cream satins. Here, to the Emmys, Angie wears a beige bustiered number with a beaded slit — an accent that would become the actresses’ red carpet signature for the next two decades.

angelina jolie in a goth dress and dark hair on the red carpet

At the Oscars, 2000

Only two years after winning the television industry’s most esteemed awards for Gia, Angie made her Hollywood breakthrough with the drama film Girl, Interrupted. Starring opposite fellow 90s babe Winona Ryder, the actress garnered critical acclaim and award nominations for her mesmerizing performance as sociopath Lisa. Perhaps inspired by the film’s dark subject matter, for the Girl, Interrupted awards show circuit, Angie returned to her favoured goth-y look — this time with a glamorous edge suited to a Hollywood award-winner. Here, to the 2000 Oscars, where she took home the award for Best Supporting Actress, Angie wears the most memorable red carpet ensemble from this era: a Morticia Addams-esque black gown with matching ‘do.


At the Gone in Sixty Seconds premiere, 2000

Off the awards show carpets, Angie’s turn-of-the-millennium style was less gothic and more biker chic. Think graphic and baby tees, singlets, blazers and duster jackets, stovepipe denim, cowboy boots, and leather, leather, leather. Remember the ultra low-rise lambskin pants she wore to the premiere of Tomb Raider? (No doubt inspired by Lara Croft, herself.) Here, with then-husband Billy Bob Thornton, the actress wears one of her quintessential Y2K outfits: a sleeveless tee with — you guessed it — a pair of leather pants. During her three year-long marriage to the actor, Angie’s outfits were accessorized with his-and-hers blood vial necklaces and, of course, her dedicated upper arm tattoo.

angelina jolie posing on the red carpet in a white silk dress

At the Academy Awards, 2004

By the mid-2000s, with both an Oscar and an action film franchise under her belt, Angie was a bonafide Hollywood leading lady. Naturally, the actress’ red carpet garb evolved to match her A-list status. During this era, Angie’s iteration of movie star glam took in strappy halter styles, wrap dresses, and gowns with plunging necklines and deep center slits. Here, to the 2004 Oscars, the she wears a very Old Hollywood-inspired gown, reminiscent of movie stars past.

angelina jolie wearing a cheetah jacket at and red stilettos

At the premiere of Shark’s Tale, 2004

The 2000s also marked a major shift in Angie’s personal life. After filming 2001’s Tomb Raider in war-torn Cambodia, Angie became a United Nations Goodwill Ambassador and began her decades-long career as a humanitarian. The following year she adopted her first son, Maddox, from Cambodia, and separated from then-husband — and Hollywood bad boy — Billy Bob Thornton. “I took charge of our life when he came home. I decided to make big choices and live even bolder […] because it was our life suddenly,” she told Barbara Walters, regarding Maddox. By 2004, Angie had a newfound lease on life — as both a mother and a humanitarian — and a more polished off-duty style to match. Now an A-list actress and a mom, Angie began wearing more sophisticated — but no less practical — garb off the red carpet. Whether attending a film premiere or hanging out with Maddox in her off-time, Angie was frequently photographed wearing jeans, trench coats, ballet flats, pencil skirts, cardigans, and massive shades to block out the flash of the paparazzi. Here, to the premiere of Shark’s Tale, Angie wears a leopard trench, bootcut jeans, pointy kitten heels and her signature blow-out.

angelina jolie posing with brad pitt on the red carpet