Beauty Evolution: Angelina Jolie
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Little Lady2 of 22
By Abby Gardner
In 1986, a young Angelina stepped out at the Academy Awards with dad Jon Voight ... and she was already making style statements. The lace, the pearls and the feathered hair were all very of-the-moment.
Teen Spirit3 of 22
This 1991 shot is about as tame as Angie's looks would be for quite a few years. She may look conservative here, but a beauty rebellion was definitely a-brewing.
Wild Child4 of 22
See what we meant about rebellion? By 1997, Angelina had re-emerged in the public eye as an actor in her own right. And one with a darker side than Hollywood was used to, as evidenced by this shaved 'do.
Dark & Stormy5 of 22
Granted the late '90s offered up some of our least favorite makeup trends, but even this heavy eye and lip combo Angelina wore to a Gia premiere was not the norm. This was a girl who didn't care whether people thought her choices were "pretty" or not.
Switch Hitter6 of 22
And just when we thought we had Angelina's look figured out, she turns up with a blonde style that was much more Marilyn Monroe than downtown punk. Little did we know she'd be keeping us guessing for years to come.
Locked Up7 of 22
One thing that's never been questioned is Angelina's ability to immerse herself in her roles, both physically and mentally. And somehow she seems to look right in any style. Even this streaky, short-bangs look from her Oscar-winning turn as the troubled Lisa in Girl, Interrupted.
All That Glitters8 of 22
We loved this sleek updo paired with a glittery silver gown that Angelina chose for the Golden Globes in 1999, where she picked up a statue for Gia.
Tainted Love9 of 22
Ah, the Billy Bob years where we enter full-on wild child phase. Jet black hair, sultry makeup, vials of blood around the neck. And I think we all remember what Billy Bob let the world know about what happened in the car on the way to this event. Needless to say, the look is straight sexy.
Hell's Angel10 of 22
Angelina looks like the prettiest biker babe we've ever seen. This look is all about length, lips and leather. And if we thought for one second that we could pull it off, we'd totally try.
Witchy Woman11 of 22
Most stars turn to old Hollywood for inspiration while getting ready for the Oscars. Angie obviously preferred the ultimate goth princess, Morticia Addams. While the whole package might not be for everyone, the makeup is really rather stunning, especially that winged eye.
On Air12 of 22
For her next role, in Life or Something Like it, Angelina morphed into a blonde television reporter ... and yet again looked totally gorgeous.
Painted It Black13 of 22
This is hands-down our least favorite version of Angelina. We just can't endorse the super painted on brows, though admittedly even those can't hide the woman's insane beauty.
Hot Mama14 of 22
When she adopted her first child, Maddox, in 2002 Angelina obviously entered a new phase, and it showed in her beauty choices, too. Everything just seemed to soften a bit.
Citizen Of The World15 of 22
Around this time, Angie also got super involved in humanitarian causes. While she's obviously focused on more important things than her hair and makeup, we are still dumbfounded as to how one can look that beautiful without even trying.
Golden Girl16 of 22
A lighter and brighter Angie continued to emerge on the red carpet. She just seemed happier ... and more highlighted.
Suited Up17 of 22
We love a business casual Angelina too. This suit and wavy updo combination seems perfect for all her trips to the UN and Congress, right?
Suburban Chic18 of 22
The retro red lips and the chignon were perfect for her character, Clover, in The Good Shepherd. But they could just as easily be worn on the red carpet today.
My Goddess19 of 22
Does it get prettier than this? We're not sure it's possible. The loose hair and the nude glossy lips are our two favorite parts. But generally speaking, we'd give just about anything to look like this for one night.
Swept Away20 of 22
With every baby Brad Pitt and Angelina add to their brood, she seems to grow more and more serenely attractive. Gone are the wild, in-your-face choices ... and we can't say we miss them all that much.
Mommie Dearest21 of 22
The Angelina we see on the red carpet now is more earth mother than tough chick, especially when she's glowing and pregnant, with her hair falling around her shoulders.
The Siren Calls22 of 22
But not to worry, she still turns up the sex appeal, just a little differently than she used to. Now all it takes is a matte red lip and a side part. Can't wait to see what's next beauty-wise. ...
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