1999

Jolie went platinum for Girl, Interrupted, but limited her beauty routine to Carmex and lotion. That said, her ultra-light hair was a sharp pivot from her naturally dark tresses—and it made a bold statement.

2000

In 2000, Jolie won an Academy Award for Girl, Interrupted, wearing Morticia Addams-like black extensions and winged eyeliner. A nude lip keeps the focus on her piercing blue eyes.

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 sensual."

2008

Pregnant with twins Knox and Vivienne, the actress glowed in a high-volume style at the Kung Fu Panda premiere. As usual, her makeup was barely there—including shimmery shadow, black liner, and a light pink lip.

2009

Nominated for her role in The Changeling, Jolie framed her face with an undone updo at the Screen Actors Guild Awards. Slightly volumized hair at the crown and matte pink lips are a nod to the '60s.

For the Cannes Film Festival premiere of Brad Pitt's Inglourious Basterds, Jolie played up her famous lips with a bright red color. Tousled, side-flipped hair keeps this beauty look from looking too overdone.

2010

Loose, voluminous locks paired with soft cat-eye liner and glossy lips are the quintessential components of Jolie's beauty look. Accessorizing with a smile adds to her allure.

2012

For the Golden Globes, Jolie played up her incredible lips with a bright crimson hue. Her slicked-back updo is left a little loose, lending a softness to this otherwise bold beauty moment.

2013

The actress attended the world premiere of her then-fiancé 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 Laurent gown with her caramel locks in a casual curl.

2016

Jolie wore her hair smooth and straight and opted for a pared-down beauty look for the Kung Fu Panda 3 Hollywood premiere at the TCL Chinese Theatre. The result is simple yet stunning, and ever so Jolie.

2017

The actress opted for retro curls and a classic red lip in 2017, which popped even more given her fair complexion. A subtle smoky eye makes for an extra sultry finish.

2019

The actress promoted her film Maleficent: Mistress of Evil with a slightly darker hair color and a classic red pout. Her dress, which has gold and silver sequins, is a masterclass in elegance.

2021

At the UK Premiere of The Eternals, Jolie was glowing. Her radiant skin, minimal makeup, and glossy ash-brown hair prove that she is a timeless beauty.