Aniston's locks - which quickly became known as 'The Rachel' - were the envy of women worldwide and one of the most popular hairstyle requests of all time.
In the years since we have followed - and envied - her honey-coloured hair in its various guises and on Monday the 44-year-old actress revealed a dramatic new hairstyle: a chin-length bob that has divided public opinion.
Here, FEMAIL tracks the changing tresses of one of Hollywood's most famous heads...
As she was: Jennifer, pictured in September, had shoulder length blonde layered locks before the chop
Smooth: Jen is known for being perfectly polished on the red carpet
Beach babe: Jennifer, pictured in August this year, is famed for her beachy locks
Making waves: Jennifer, pictured in 2011, rocked a pretty, tousled style
Bottle blonde: The actress, in July 2011, opted for summery blonde highlights
Been there before: Jennifer tried out a shorter style with a faux-bob back in May 2011
Rich hues: The star, pictured in March 2010, sported her trademark locks with a darker tone
Bedhead: Jennifer in 2007 rocked a messy, light brown do to the People's Choice Awards
So far, no regrets for the Hollywood actress, who has been engaged to her Wanderlust co-star Justin Theroux for over a year.
'I did it! I feel great. I feel lighter,' said the beauty, who had six inches taken from her hair.
'It’s simple, it’s really simple, that’s for sure. But I’m always one of those girls who does a big old chop just to get it really healthy, to repair all the [damage from] hair coloring and stuff like that. And I just got bored, honestly. It’s fun to change it up once in awhile.'
Celebrity hairdresser Michael Van Clarke said: 'I think the idea of Jennifer in a shorter layered bob can work very well, but as with any cut, it’s all in in the detail.
'The way the hair has been layered will make it more unpredictable for her. So some days she'll love it and some days she may want to kill her hairdresser!'.
Angel Montague-Sayers , UK Creative Ambassador for Cloud Nine, added: 'Jennifer Aniston's new blunt hair cut is a dramatic change from her well known softer, layered 'Rachel' look. I think Jennifer suits softer more textured hairstyles which soften her features and work well with her face shape.
'She
could possibly rock the style better by adding some movement and texture
to the cut either by adding soft light layers along the edge to soften
the blunt cut.'
Nearly brunette: Pictured at the ShoWest Awards 2005, Jennifer opted for a near brunette colour
Darker and darker: Back in 2003, she rocked a deeper colour
Au natural: She let her usually smooth locks embrace their natural curl in 2002 at the Emmy Awards
Short style: Jennifer rocked short locks back in January 2002 - a style she is currently revisiting
Up do: Jen proved that she can look great with a messy bun on the set of Picture Perfect
Oomph! Jennifer showcased a voluminous bob at an event in 2001
The Rachel: This is the iconic hairstyle that defined the 90s and became one of the most requested ever
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