See Angelina Jolie’s Beauty Transformation Through the Years
Angelina Jolie’s philosophy when it comes to both her wardrobe and beauty looks could be summed up as “if it ain’t broke, don’t fix it.” For years now, the latter has consisted of blowout brunette locks, winged eyeliner, and either neutral or a bold red lip. But that wasn’t always the case with the 46-year-old Academy Award winner, who was just a teen when she kicked off her career. By the late ‘90s, when she won a Best Supporting Actress Oscar for her role in Girl, Interrupted, Jolie had experimented with everything from sculpted eyebrows to blue eyeshadow to a shaved head. Take a look back at those early alt days and see how her look transformed up to the glamorous present ahead of her 47th birthday on June 4.
1991
Jolie was just 16 when she curled her hair for this portrait session at the very start of her career.
1994
She came to embrace thin, sculpted brows, otherwise opting for a natural look.
1997
From there came an alt phase that saw Jolie repeatedly change up her hair.
1997
It was just shy of a buzzcut at the New York premiere of Playing God.
1998
Jolie toned down the edginess of her pixie cut—and paired it with blue eyeliner—at the 55th annual Golden Globe Awards.
1999
She made another major transformation, this time into a blonde, at the 56th annual Golden Globe Awards.
1999
She stuck with the look—and elevated the glamour—at the 1999 Screen Actors Guild Awards.
1999
Jolie’s thin, sculpted eyebrows were in their heyday when she attended the L.A. premiere of Girl, Interrupted.
2000
From there, she went with a blueish-grey hue, seen here at the 57th annual Golden Globe Awards.
2000
Jolie went full-on goth with jet black hair and her most dramatic winged eyeliner yet at the 72nd annual Academy Awards.
2000
And toned down the eyeliner at the 6th annual Screen Actors Guild Awards.
2001
The dye stuck around at the Los Angeles premiere of Original Sin.
2003
Jolie experimented with bangs at the New York premiere of Beyond Borders.
2004
She began to embrace her current natural glowing look, topped off with winged eyeliner, around 2004, here at the Los Angeles premiere of Sky Captain and the World of Tomorrow.
2005
Jolie went with a neutral lip for the Los Angeles premiere of Mr. and Mrs. Smith.
2007
She paired her unmissable yellow dress with a glamorously messy updo at the Cannes Film Festival premiere of Ocean’s Thirteen.
2008
Her glowing locks at the 14th Annual Screen Actors Guild Awards looked straight out of a haircare commercial.
2009
Jolie teased her hair at the 81st annual Academy Awards, the better to show off her emerald jewels.
2010
She returned to bangs—this time with highlights—at the London premiere of Salt.
2012
Jolie was all glamour with a bold red lip at the 84th annual Academy Awards.
2012
She reprised the look later that awards season, at the 2012 Golden Globes.
2014
Again putting the focus on her statement earrings, Jolie slicked her hair back into a ponytail at the Los Angeles premiere of Maleficent.
2016
She was almost entirely fresh-faced at the Los Angeles premiere of Kung Fu Panda 3, the sole exception being her winged eyeliner.
2017
The next year, she piled on the mascara for an appearance at the Toronto Film Festival premiere of The Breadwinner.
2018
Jolie returned to a darker hued hairstyle at the 75th Annual Golden Globe Awards.
2018
She went with a less conventional shade of red lip at the 23rd annual Critics’ Choice Awards.
2018
Jolie fulled off the full length of her lashes by clicking her hair at the back EE British Academy Film Awards.
2019
The actor looked radiant with an ever-so-slightly highlighted blowout at the Maleficent: Mistress Of Evil premiere in Rome.
2021
She changed it up with glossy bright red lipstick at Variety annual Power of Women event in 2021.
2021
The next month, she turned up to the L.A. premiere of Eternals with sculpted brows and a gold chin cuff.
2021
And at the movie’s Rome Film Fest premiere just eight days later, she was back to her classic look, this time with wavy, shorter hair.
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