The natural brunette (and natural beauty) graduated from N.Y.C.'s LaGuardia High School of Music and Art.
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Aniston landed TV roles in Molloy and Ferris Bueller.
For the Leprechaun premiere, the actress wore her mahogany locks in long layers and sported ultra-'90s brick lipstick.
The wavy-haired star got her breakout role as Rachel Green on Friends.
The cut that launched a thousand layers! "This was the original Rachel, with layered shoulder-length hair," said hairstylist Chris McMillan.
A newly-minted movie star with 'Til There Was You and Picture Perfect, Aniston brought the focus to her bright blue eyes with smudged liner and an understated updo.
The Office Space star tried wild-child faux dreads for the Emmy Awards. "Jen's adventurous side-she did this look once and never went there again," said makeup artist Robin Siegel.
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"The one and only time I cut her hair short," McMillan said of this wavy bob. "She wanted to do something different."
For the People's Choice Awards, the Rock Star actress wore her sleek cut straight.
Classic Jen: sun-kissed long layers and sheer, rosy makeup.
A bronzed glow and honeyed highlights accentuated the Bruce Almighty star's sea-blue eyes.
Aniston hit the Golden Globes with beachy waves set off by a deep side-part.
"There's such a freshness about her look," said makeup artist Angela Levin of The Break-Up star. "She likes clean, glowing skin with soft, neutral makeup."
"Her dress had a '60s mod feel, so we did bone-straight hair to match," said hairstylist Richard Marin.
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Aniston wore her hair in a pony with face-framing tendrils.
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Aniston starred in He's Just Not That Into You and set trends with her Oscars hairline braid.
Aniston rocked a deep side part at an N.Y.C. event.
Aniston set trends at the Golden Globes with her piecey waves and honey highlights.
Aniston sported beachy waves anchored by a bobby pin.
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The actress switched up her look for a Bounty Hunter premiere with an easy updo.
The Just Go With It star rocked a sleek new cut courtesy of Chris McMillan. "I call it a hairline bob that follows the jawline down," the stylist told Allure. "It's angled and inspired by Vidal Sassoon haircuts and Julie Christie from Shampoo."
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Long, honeyed strands, but for how much longer? "I've been thinking about dyeing my hair a dark brown because I feel it would be healthier - it's my my natural color," our March cover girl told us.
For the People's Choice Awards, the actress opted for a classic beauty look. "I like to call it 'California babysitter hair' - it's that hair I always thought was cool when the sitter came over," said Aniston's hairstylist Chris McMillan. Aniston's makeup artist Angela Levin used the star's edgy ensemble as a starting point for her silvery eye makeup. "The inspiration was 'bad girl in a pretty dress,'" she said. Levin applied Chanel's Illusion D'Ombre shadow in Mirifique to her upper lids, then layered the brand's Quadra Eye Shadow in Vanites on top, starting with the dark purple as liner.
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The We're the Millers star swept her enviable locks to one side for the film's Berlin premiere.
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The actress dyed her tresses darker and went for a very on-trend lob at the Living Proof Style Lab in Boston.
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Aniston goes back to her roots with light brown tresses.
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The Cake star shows off her bouncy blowout at this year's SAG Awards.
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Aniston swept her hair back into a playful pony for an appearance at the Zoolander 2 premiere.
The Friends alum wore her famous highlighted locks in a beachy blowout, polishing off the look with peach lipgloss.
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The 48-year-old's loose waves complimented her chandelier earrings.