BEAUTY EVOLUTION

See Angelina Jolie’s Beauty Transformation Through the Years

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Angelina Jolie
Photo by Kostas Alexander/Fotos International via Getty Images

Angelina Jolie’s philosophy when 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 watch her look transform up until the glamorous present.

1991
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Jolie was just 16 when she curled her hair for this portrait session at the very start of her career.

1994
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Jolie came to embrace thin, sculpted brows, otherwise opting for a natural look.

1997
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Jolie entered her alt phase around 1997, repeatedly changing up her hair.

1997
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Jolie’s hair was just shy of a buzzcut at the New York premiere of Playing God.

1998
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Jolie toned down the edginess of her pixie cut—and paired it with blue eyeliner—at the 55th annual Golden Globe Awards.

1999
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Jolie made another major transformation, this time into a blonde, at the 56th annual Golden Globe Awards.

1999
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She stuck with the look—and elevated the glamour—at the 1999 Screen Actors Guild Awards.

1999
Photo by Jim Smeal/Ron Galella Collection via Getty Images

Jolie’s thin, sculpted eyebrows were in their heyday when she attended the L.A. premiere of Girl, Interrupted.

2000
Photo by Jim Smeal/Ron Galella Collection via Getty Images

From there, Jolie went with a blueish-grey hue, seen here at the 57th annual Golden Globe Awards.

2000
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Jolie went full-on goth with jet black hair and her most dramatic winged eyeliner yet at the 72nd annual Academy Awards.

2000
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Jolie toned down the eyeliner at the 6th annual Screen Actors Guild Awards.

2001
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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

Jolie 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
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Jolie went with a neutral lip for the Los Angeles premiere of Mr. and Mrs. Smith.

2007

Jolie paired her unmissably yellow dress with a glamorously messy updo at the Cannes Film Festival premiere of Ocean’s Thirteen.

2008

Jolie’s 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

Jolie 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

Jolie slicked her hair back into a ponytail at the Los Angeles premiere of Maleficent, again putting the focus on her statement earrings.

2016

Jolie was almost entirely fresh-faced at the Los Angeles premiere of Kung Fu Panda 3, the sole exception being her winged eyeliner.

2017
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Jolie 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

Jolie went with a less conventional shade of red lip at the 23rd annual Critics’ Choice Awards.

Jolie fulled off the full length of her lashes by clicking her hair at the back EE British Academy Film Awards.

2019
Photo by Franco Origlia via Getty Images

Jolie looked radiant with an ever-so-slightly highlighted blowout at the Maleficent: Mistress Of Evil premiere in Rome.