The Makeover Timeline: See Jennifer Aniston’s Transformation

Wendy Rodewald
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The Makeover Timeline: See Jennifer Aniston’s Transformation
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Jennifer Aniston's best hair looks | @stylecaster

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?

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1997

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

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1998

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

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1998

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

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1999

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

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2000

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

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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!

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2006

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

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2006

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

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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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