Beauty Evolution: Jennifer Aniston

Follow Jennifer Aniston through nearly 20 years in the spotlight. From "The Rachel," and through "The Breakup" witness the beauty hits and misses that have brought her to her present state of gorgeous.

- by Melissa Goldberg

Barry King, WireImage | Kristian Dowling, WireImage

In this 80's meets 90's look, Jennifer combines big Flashdance hair with matte makeup. The emerging star already radiates the confidence of a big Hollywood contender, even though her most famous days are still years ahead of her.

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Showing her darkest side at the "Leprechaun" premiere after party, Jennifer goes for a rich chocolate hair shade and classic 90's-style matte brown-red lipstick. But how can we blame her? We were all doing it too – thanks to Beverly Hills 90210's Brenda Walsh.

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Sporting the famous 90's "McDonald's 'M' arch in her bangs, Jennifer throws a few thin highlights in to frame her face. The lipstick is softer and creamier and not as harsh a shade. But Ms. Aniston still has a ways to go before her hair starts making headlines - which it will in just months!

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The flippy layered cut that launched a thousand copy-cats: the classic Rachel 'do. With layers that frame the face and highlighted pieces that draw you right into her eyes, it's no wonder this became the universal cut for a whole generation.

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Growing her hair out to a manageable shoulder length, Jennifer shows us that the Rachel layer cut works just as beautifully with longer locks – the key is that tight frace frame. But we're a little distracted by her over-lined bottom lip; paired with this strong red lipstick, it's looking a little clownish.

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Now Hollywood's It Girl, Jennifer plays the part with a sweeping updo and rich, warm makeup shades that reveal her more glamorous side at a Cosmo magazine party. Her thin, stripey highlights set a color trend that women imitate for years to come.

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Putting her flat iron aside for the night, Jennifer shows us that corkscrew curls are just as sexy at the premiere of "The Object of My Affection." An established star now, she amps up the makeup by tight-lining her eyes and wearing a soft red lipstick.

Jim Smeal, WireImage

Trying to break out from the layered cut, Jennifer grows her hair out for the Premiere of Scream 2. But without the load of layers that added volume and body to her hair, her strands fall flat and limp. She does get points for throwing out the heavy 90's lipstick and going softer on the makeup, though.

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Time to chop it off and start fresh! Reinventing the Meg Ryan shag, Jennifer keeps the length a little longer and the layers wavy for a sexy, run-your-fingers-through-her-hair touchable look. Her soft makeup palette of natural pinks compliments the low-maintenance vibe.

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