• 1990

    Aniston scored her first television role in the short-lived 1990 series Molloy, but her second job was way cooler (if equally brief): She played Ferris's sister Jeannie on the Ferris Bueller TV series.

    Photo: Getty Images
  • 1992

    Jen's first film role was in the campy horror flick Leprechaun. Later that year, the actress had a nose job to fix a deviated septum — but the surgery was done incorrectly. Twelve years later she had it fixed.

    Photo: Getty Images
  • 1994

    Aniston got her big break playing Rachel Green on Friends. Hair stylist Chris McMillan — who works with Aniston and remains a good friend to this day — created her layered haircut, which became a major trend. Aniston herself wasn't a fan of the "Rachel": "It was the ugliest haircut I've ever seen," she told Allure in 2011.

    Photo: Getty Images
  • 1997

    Jen sported a dreadlocked 'do at a VH1 event. Maybe she was inspired by dread-headed Counting Crows singer Adam Duritz, who she dated a few years earlier?

    Photo: Getty Images
  • 1997

    A sleeker look — complete with a classic updo — proved to be a better fit.

    Photo: Getty Images
  • 1998

    Jen sported loose ringlets for an appearance in 1998. Wonder if she "scrunched"?

    Photo: Getty Images
  • 1998

    To be fair, wearing your hair like this was a thing in the late '90s.

    Photo: Getty Images
  • 1999

    Again with the dreadlocks! This Emmys 'do might be the reason Jen sticks to her signature look these days.

    Photo: Getty Images
  • 2000

    Brad and Jen became an item in 1998 and married in 2000. For awhile, they were the hottest couple in Hollywood.

    Photo: Getty Images
  • 2001

    Aniston chopped her hair to shoulder length — and totally pulled it off.

    Photo: Getty Images
  • 2004 

    By the time Friends ended, Jen was already starring in films. At the premiere of Along Came Polly, she sported side-swept bangs.

    Photo: Getty Images
  • 2005

    Pitt left Aniston for Angelina Jolie in 2005 — but hey, looking good is the best revenge. Team Jen!

    Photo: Getty Images
  • 2006

    Jen looked radiant at the premiere of The Break-Up, in which she co-starred with real-life love interest Vince Vaughn.

    Photo: Getty Images
  • 2006

    Aniston and Courteney Cox have been besties since they worked together on Friends. We're pretty sure they trade hair tips, too.

    Photo: Getty Images
  • 2009

    We still love the braided hairstyle Jen wore to the Oscars in 2009.

    Photo: Getty Images
  • 2010

    For her first foray into the beauty business, Jen launched her signature fragrance, Jennifer Aniston, in 2010.

  • 2011

    We love Aniston in a cute pair of glasses.

    Photo: Getty Images
  • 2011

    Aniston chopped her hair again, and we're pretty sure this style singlehandedly kicked off the "lob" trend of the past couple years.

    Photo: Getty Images
  • 2012

    Aniston joined hair product brand Living Proof as a spokesperson and co-owner. She also brought her longtime stylist Chris McMillan to the company.

  • 2013

    Another beauty deal! Jen became the face of Aveeno earlier this year.

  • 2013

    Over the summer, Jen sported an edgy cornrow braid.

    Photo: Getty Images
  • 2013

    Aniston has been looking as radiant as ever on her recent press tour for We're The Millers.

    Photo: Getty Images
  • 2013 We're loving this side parted look. Who says Jen never changes it up?  

    Photo: Getty Images

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The Makeover Timeline: See Jennifer Aniston’s Transformation


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