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ake a look at Angelina Jolie ‘s filmography, and you might never believe that the woman who has transformed herself into iconic — and instantly identifiable — characters like Lara Croft, Maleficent, and Gia Carangi has a strong signature beauty look all her own.
Although her IMDb page would suggest that Jolie is game to try any and every hair color, cut, and style an on-set hairdresser could dream of, the actress and humanitarian’s red-carpet look is almost always relegated to the simple and classic. And in an age of being extra with every aspect of your routine, there’s something to be said for Jolie’s knack for being consistently low-key without ever missing a beat.
To honor the modern icon’s beauty evolution, we rounded up Jolie’s best looks from 1998 to 2018, ahead.
Just because 1998 was the first year Jolie was nominated for a Golden Globe didn’t mean she was prepared to play it safe on the red carpet. Back before her days of subtle trims and bare-faced makeup, Jolie was the ’90s beauty risk-taker of our dreams — teal eyeshadow and all.Photo: Frank Trapper/Corbis/Getty Images.
Two years later, we got a glimpse of Jolie during her short-lived, albeit memorable, goth years — you know, not too long before she was wearing a vial of Billy Bob Thornton’s blood around her neck. Still, whirlwind relationship aside, Jolie’s daring look meant back-grazing jet-black hair, smoky lash lines, and cat-eyes so sharp Kat Von D would be jealous.Photo: Steve Granitz/WireImage.
Fast forward to 2004 in Cannes, and Jolie briefly ditched her dark roots for something brighter. Thanks to a few sun-kissed highlights, Jolie’s look was less gloomy badass and more Hollywood It-girl.Photo: Tony Barson Archive/WireImage.
That same year, Jolie broke out a signature hairstyle that we’d see for years to come: the half-tied updo featuring loose tendrils. This was also around the same time fans began to notice that little to no makeup at all was Jolie’s red-carpet comfort zone — and it worked.Photo: Gregg DeGuire/WireImage.
Catching a vibrant color on Jolie’s lips is a sight to behold, because in her two decades in the spotlight, the actress rarely ever goes for something vivid. But this appearance was one of her first exceptions, and paired with a glowing complexion and a small streak of eyeliner, Jolie made “no-makeup” makeup a new trend worth trying.Photo: Jeffrey Mayer/WireImage.
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