1987: The natural brunette (and natural beauty) graduated from NYC’s LaGuardia High School of Music and Art.
1990: Aniston landed TV roles in “Molloy” and “Ferris Bueller.”
1992: For the “Leprechaun” premiere, the actress wore her mahogany locks in long layers and sported ultra-’90s brick lipstick.
1994: The wavy-haired star got her breakout role as Rachel Green on “Friends.”
1995: The cut that launched a thousand layers! “This was the original Rachel, with layered shoulder-length hair,” said hairstylist Chris McMillan.
1997: 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.
1999: 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.
2000: “The one and only time I cut her hair short,” McMillan said of this wavy bob. “She wanted to do something different.”
2001: For the People’s Choice Awards, the “Rock Star” actress wore her sleek cut straight.
2002: Classic Jen: sun-kissed long layers and sheer, rosy makeup.
2003: A bronzed glow and honeyed highlights accentuated the “Bruce Almighty” star’s sea-blue eyes.
2004: Aniston hit the Golden Globes with beachy waves set off by a deep side-part.
2006: “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.”
2007: “Her dress had a ’60s mod feel, so we did bone-straight hair to match,” said hairstylist Richard Marin.
2009: Aniston starred in “He’s Just Not That Into You” and set trends with her Oscars hairline braid.
2010: The actress switched up her look for a “Bounty Hunter” premiere with an easy updo.
Source : Yahoo