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

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

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, Jolie became one of the world's best-known stars, from cult classics such as Girl, Interrupted to blockbusters such as Lara Croft: Tomb Raider. 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 sophisticated, minimalist fashion choices that reflect her allure. On the actress' 48th birthday, we look back on young Jolie's best fashion style moments.

1 / 21

people:cb1 los angeles:cb2 angelina jolie:cb3 formal wear suit dress person fashion adult bride female woman man

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.

half-length:cb1 computer hacker:cb1 celebrities:cb2 angelina jolie:cb3 jonny lee miller:cb1 coat jacket face person photography portrait boy child male people

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 colour seen so far on Jolie at this point, she embraces her “dark” demeanour 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.

beverly hills california dress evening dress formal wear finger person fashion gown adult bride woman

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

t317203 film actress head & shoulders evening wear fashion & clothing single female people film subject colour picture attribute photograph image type new york ny blonde person dress adult female woman portrait fashion formal wear smile

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

beverly hills california finger hand person cosmetics perfume adult female woman face head

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.

screen actors guild award 5th annual awards shrine auditorium los angeles ca angelina jolie award diamond necklace clothing dress formal wear accessories evening dress finger lady necklace fashion face

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.

world premiere celebrities celebrity "girl interrupted" los angeles ca angelina jolie actress coat fashion long sleeve jacket person adult male man face overcoat

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.

human relationships:cb2 smiling:cb1 caucasian ethnicity:cb2 movie premiere:cb2 red carpet:cb2 male:cb2 female:cb2 celebrities:cb2 american:cb2 los angeles:cb2 angelina jolie:cb3 billy bob thornton:cb3 june 2000:cb1 fashion person skin tattoo adult female woman hat face premiere

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.

full length beverly hills california fashion adult female person woman premiere red carpet coat face shoe

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.

windsor long sleeve blouse person pants car alloy wheel shoe grass face lawn

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

black:cb1 half-length:cb1 portrait:cb2 prominent persons:cb2 tattoo:cb1 caucasian ethnicity:cb2 movie premiere:cb1 red carpet:cb1 female:cb2 pants:cb1 american:cb2 belt:cb1 t-shirt:cb1 los angeles:cb1 angelina jolie:cb3 lara croft: tomb raider (2001 movie):cb2 leather pants:cb1 june 2001:cb1 mann's village theater:cb1 fashion adult female person woman accessories glasses face tie belt

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.

beverly hills california fashion adult female person woman premiere male man necklace glasses

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.

red shoes wearing celine new york city new york clothing coat pants person shoe overcoat jeans high heel fashion long sleeve

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.”

not applicable cannes clothing lifejacket vest transportation vehicle watercraft hosiery sock person pants

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.”

cannes adult female person woman paparazzi male man suit glasses face

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

2 shot hollywood california fashion formal wear adult female person woman dress male man suit

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.

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