1991
As
a student at Beverly Hills High School, Jolie was an unknown quantity.
"I wore black boots with big silver bat [charms] that dragged when I
walked," Jolie has said. "I wasn't aware of how I looked, but apparently
I looked really
1998
The pixie-cropped actress won her first Golden Globe for TV biopic George Wallace; the following year she would receive a second statuette for her role in Gia.
1999
She went platinum for Girl, Interrupted, but limited her beauty routine to Carmex and lotion.
2000
She won an Academy Award for Girl, Interrupted wearing Morticia Addams-like black extensions and winged eyeliner.
2003
The Beyond Borders star, and new mother to adopted son Maddox, lightened up both her locks and makeup for a fresh look.
2004
The Alexander actress went for Old Hollywood glam with long retro curls and arched brows.
2005
The
glamorous mom—who would expand her brood with daughter Zahara and
become pregnant with Shiloh—sported a voluminous '60s-inspired mane
and liquid liner to the Mr. and Mrs. Smith premiere.
2007
For the Golden Globes, the A Mighty Heart
star (and mom to the newly-adopted Pax) rocked a sleek bouffant updo.
"Angelina loves wearing her hair away from her face," hairstylist
Ted Gibson has said.
2007
"Her
mouth is so large and beautiful," makeup artist Janeen Schreyer has
said of the born beauty. "I usually don't color it." Hairstylist Ted
Gibson shows similar restraint: "She loves to keep a natural wave in
her hair. It's more
2008
Pregnant with twins Knox and Vivienne, the actress glowed in a high-volume style at the Kung Fu Panda premiere.
2009
Jolie enhanced her baby blues with liquid liner at the Golden Globes.
2009
Nominated for her role in The Changeling, she framed her famous face with an undone updo at the Screen Actors Guild Awards.
2009
For the Cannes Film Festival premiere of Brad Pittâs Inglourious Basterds, Jolie played up her famous mouth with bright red lipstick.
2010
Classic Angelina: Loose, voluminous locks with soft cat-eye liner and glossy lips.
2011
Jolie looked characteristically stunning at the Golden Globes.
2012
Wow! For the Golden Globes, Jolie played up her incredible lips with a bright crimson hue.
2013
The actress attended the world premiere of fiance Brad Pitt's movie World War Z just weeks after she revealed she underwent a preventative double mastectomy. She wowed the crowd in a black, floor-length Saint
2014
Jolie brightens up her hair with an auburn hue.
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