1990
Aniston landed TV roles in Molloy and Ferris Bueller.
1992
The starlet looked like a different person after changing her hair colour from light brown to brownish-black.
Angelina Jolie’s transformation through the years
Bang on trend, Aniston often sported the ultra-'90s brick lipstick.
1995
The cut that launched a thousand layers! From long hair to a layered bob – this fashionista has always been daring with her choices. She was indeed the pioneer of the Rachel cut!
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.
2000
"The one and only time I cut her hair short," her longtime hairstylist Chris McMillan said of this wavy bob. "She wanted to do something different."
2002
Classic Jen: sun-kissed long layers and sheer, rosy makeup.
2006
"There's such freshness about her look," said makeup artist Angela Levin of The Break-Up fame. "She likes clean, glowing skin with soft, neutral makeup."
2009
Aniston starred in He's Just Not That Into You and set trends with her Oscars hairline braid.
2014
The actor dyed her tresses darker and went for a very on-trend lob at the Living Proof Style Lab in Boston.
2018
She went back to her blonde streaks, beachy waves and long hair.
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