1June 19, 1990
Getty ImagesAniston as Jeannie Bueller, never forget.
2January 6, 1992
Getty ImagesWhen you're ambivalent about your new bangs.
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3June 15, 1994
Getty ImagesBehold, the first iteration of "The Rachel" from the year that Friends debuted on television.
41995
Getty Images"I think it was the ugliest haircut I've ever seen," Aniston told Allure in 2011 of Rachel Green's polarizing hairstyle.
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5January 1, 1995
Getty Images"It was a really fun cut and different to anything else around at the time. It was an easy cut, but it needed regular trims to keep the layers looking sharp," says hair stylist Chris McMillan of his famous "Rachel" cut.
6June 4, 1995
Getty Images"It's high-maintenance, not a wash-and-go style. You need to blow-dry with a round brush to help define all those flicks," McMillan adds.
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71996
Getty ImagesAniston straightens her layers through the growing out phase.
8July 19, 1997
Getty ImagesAniston gives her blow dryer a break for the premiere of Picture Perfect.
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9July 23, 1997
Getty ImagesHere, a sleek chignon to celebrate her Cosmopolitan cover.
10April 9, 1998
Getty ImagesProm ringlets at the premiere of The Object Of My Affection.
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11April 15, 1998
Getty Images 12September 12, 1999
Getty ImagesNot pictured: ultimate '90s Emmy Awards date, Brad Pitt.
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13October 23, 1999
Aniston experiments with ropey surf-waves.
14March 26, 2000
Getty ImagesHair extensions are actual magic.
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15December 11, 2000
Getty ImagesBlunt bob, but make it wavy.
16January 7, 2001
Getty ImagesAniston at the People's Choice Awards with a blunt bob (that would later become the standard issue Jenner-Hadid haircut of Summer 2017).
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17November 19, 2001
Getty ImagesAniston returns to the angled look she debuted in 1996.
18January 20, 2002
Getty ImagesIt's impossible to distinguish Jen from Brad at this point.
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19September 22, 2002
Getty ImagesA rare curly hair moment for Aniston's first Emmy win.
20June 6, 2002
Getty ImagesAt the premiere of Bourne Identity giving very few f*cks.
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