Young Angelina Jolie's Best '90s and Y2K Fashion Moments

On actress and humanitarian Angelina Jolie's 48th birthday, L’OFFICIEL looks back to the beginning of Jolie's budding career and her on-point style in the late '90s and early noughties.

Photos: Getty Images

Since the beginning of Angelina Jolie’s prolific career in the late 1980s, the American actress and humanitarian has long been praised for her almost supernatural good looks, and her style is no different: Jolie’s wardrobe reflects her innate sophisticated persona.

Following critical and commercial film success, from cult-classics such as Girl, Interrupted to blockbusters such as Lara Croft: Tomb Raider, Jolie became one of the world’s best-known stars. In using her platform as a household name to speak out on behalf of human rights, child poverty, and sexual violence in conflict-torn regions, Jolie’s compassion is prominent in all aspects of her private and public life.

Throughout her career, Jolie has set the tone with sohisticated, minimalist fashion choices that reflect her allure. On the actress' 48th birthday, look back on young Jolie's best fashion style moments.

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In 1986, an 11 year old Jolie arrives at the 1986 Academy Awards with her father, actor Jon Voight, and brother, James Haven. The future star is dressed in pearls and a lace puff sleeve dress.

In 1991, Jolie is once again pictured alongside her now estranged father, Voight, at the reopening of “Tru.” Wearing an oversized blazer, matching trousers, a silk tank top, and pearl necklace, Jolie embodies her love of classic minimalist elegance.

In 1991, Jolie is once again pictured alongside her now estranged father, Voight. Wearing an oversized blazer, matching trousers, a silk tank top, and pearl necklace, Jolie embodies her love of classic minimalist elegance

At the 25th anniversary of “Midnight Cowboy,” Jolie introduces yet another pillar of her unfaltering style. In elements of ‘90s gothic influences, Jolie sports a black leather blazer as she poses with her brother, who is similarly dressed in a monochromatic black ensemble.

At the 25th anniversary of “Midnight Cowboy,” Jolie introduces yet another pillar of her unfaltering style. In elements of ‘90s goth influences, Jolie sports a black leather blazer as she poses with her brother, who is similarly dressed in a monochromatic black ensemble.

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In 1995, posing to promote her film “Hackers,” her first leading role in a major film, Jolie sports a pixie cut, illustrating her ability to rock any hair style.

In a Jolie staple, the actress wears satin to the 1997 Cable ACE Awards. Matching her aforementioned elegant grey satin slip dress with a velvet cape, and the darkest hair color seen so far on Jolie at this point, she embraces her “dark” demeanor that was previously criticized in her early career.

Bringing her love of smart business wear to the red carpet once again, Jolie poses with fellow movie star Ryan Phillippe at the 1998 premiere of “Playing by Heart” in a structured cream coat, natural makeup, and sleek pulled back hairdo.

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Donning a strapless sequined gown, Jolie brings an element of dramatic glam with darker gothic eye makeup to the 55th Annual Golden Globe Awards.

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In 1998 in New York, Jolie swaps her dark locks for a fresh, tightly curled blonde look.

Jolie wins yet another Golden Globe, her second in a row, for what many consider her breakout role as Gia in the biographical drama of the same name. Playing Gia Carangi, the fashion model who tragically died after contracting HIV, the actress was praised for her performance.

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Similarly, during the very same awards season for “Gia,” Jolie wins her first Screen Actors Guild Award. Attending the 5th annual award ceremony, Jolie once again exudes effortless elegance in a simple, off-the-shoulder white gown.

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Following her mass acclaim for “Gia,” Jolie is cast in the supporting role as Lisa in “Girl Interrupted” opposite Winona Ryder. Promoting her bad-girl role, Jolie returns to her naturally darker locks, as she rocks low-rise leather trousers with a black crop top to the world premiere of the film in Los Angeles in 1999. The simple, yet communicative look, is matched with gothic makeup.

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With film co-star and future husband Billy-Bob Thornton, the star attends the Los Angeles Premiere of “Gone in 60 Seconds.” Jolie embraces simplicity, wearing a simple grey t-shirt hiked up over her shoulder to show off her newest tattoo of her co-star’s name.

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In 2000, Jolie attends the 2000 Golden Globes Awards at the Beverly Hilton Hotel with her brother, James Haven, in a floor-length pale slip.

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Wearing a smart sartorial monochromatic white outfit, Jolie attends Cartier’s Polo match.

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Wearing all black with the very Y2K look of low-rise jeans, Jolie yet again embraces gothic elements, as she embodies her titular role as Lara Croft, badass- video game character at the Los Angeles Premiere of the film in 2001.

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Jolie and Thornton walk the red carpet for the 59th Annual Golden Globe Awards in 2002. Wearing a strapless black satin dress and simple diamond necklace, Jolie was praised by many for bringing mature grown-up sophistication to the red carpet.

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A true Y2K look with an elegant spin: the recently chestnut-haired bombshell wears the ever-popular cheetah coat, flared jeans, and red kitten-heels to the New York Premiere of a “Shark Tale.”

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A very off-duty look, Jolie and Will Smith are photographed at the Carlton Beach Pier in Cannes, wearing t-shirts and jeans under life-jackets while sitting on a blow-up beach toy to promote their film “Shark Tale.”

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At the premiere of “Shrek 2” Jolie wears a sophisticated updo, with a masculine suit with oversized collars.

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At the “Sky Captain and the World of Tomorrow” premiere, Jolie wears a slip dress and red satin peep-toes while holding a singular white role.

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At the Los Angeles Premiere of “Mr & Mrs. Smith,” in which Jolie plays opposite her future husband Brad Pitt, Jolie wears her hair slicked back to highlight her figure-hugging leather gown.