Ashlee Simpson's Changing Looks

By Instyle
Updated Sep 30, 2016 @ 10:15 am
Jason LaVeris/Getty

Ashlee Simpson's Changing Looks

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1 of 20

2001

SGranitz/WireImage

With her long blond braids and trendy hat, the backup dancer (and Malcolm in the Middle guest star) could have doubled for her famous sister.

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2 of 20

2003

Jean-Paul Aussenard/WireImage

Simpson wore her hair in a choppy shag for her role as Cecilia in 7th Heaven.

3 of 20

2004

Vince Flores/Celebrity Photo

"When Autobiography came out, she really wanted to differentiate herself from Jessica," said her mother Tina Simpson. "That was the purpose of the dark hair, and there is that dark side to Ashlee."

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4 of 20

2005

Ray Williams/Celebrity Photo

Colorist Rita Hazan brought the singer back to golden blond ("It was a celebration of her tour ending") and hairstylist Oscar Blandi called the chop "sexy, rock and roll-perfect for her."

5 of 20

2005

Laura Cavanaugh /Landov

Simpson released her second album, I Am Me, and visited Gwen Stefani's colorist. "I was like, who has good bleached hair?" she said of her retro style. "I've gone through all the hair colors!"

6 of 20

2005

John Shearer/WireImage

The rock and roller wore her hair in a funky angled bob for the Billboard Music Awards.

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7 of 20

2006

Mike Flokis/Headpress/Retna

A blond Simpson wore her hair in piecey rocker chic waves.

8 of 20

2006

James Devaney/WireImage

Simpson starred in Chicago on Broadway with a pared-down nose. Although the entertainer never officially confirmed the rhinoplasty, she admitted that the surgery was obvious "as long as people have two eyes."

9 of 20

2007

Chris Weeks/WireImage

The multi-talented star looked every inch the Hollywood glamour girl with waist-length waves and her favorite smoky eye makeup.

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10 of 20

2008

Jeffrey Mayer/WireImage

Simpson rocked piecey fringe and red hair in Vegas.

11 of 20

2008

Celebrity Photo

A big year: the redhead released her third album Bittersweet World, married Fall Out Boy bassist Pete Wentz and gave birth to son Bronx Mowgli.

12 of 20

2009

Jordan Strauss/WireImage

Simpson joined the cast of the brand-new Melrose Place.

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13 of 20

2010

Clint Spaulding/PatrickMcMullan.com/Sipa Press

Simpson rocked ombre locks for New York Fashion Week.

14 of 20

2010

Jen Lowery/Splash News

Simpson debuted a razored platinum pixie.

15 of 20

2011

Imeh Akpanudosen/Getty Images

Longer and lighter, her cute crop takes on a new shape.

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16 of 20

2012

Kevin Mazur/WireImage

Simpson swept her coif into a retro wave for the SAG Awards.

17 of 20

2013

FilmMagic

Somebody definitely called in the glam squad for this look. Simpson attended the Los Angeles Premiere of The Hunger Games: Catching Fire with her hair styled in a side-swept, ultra glam look and finished the look with a sultry smoky eye.

18 of 20

2014

FilmMagic

Upon arriving at the Los Angele Premiere The Hunger Games: Mockingjay Part 1, Simpson showed off her natural beauty with lightly styled hair and soft, subtle makeup.

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19 of 20

2015

Getty Images North America

Simpson returned to her platinum-blonde signature look and kept her makeup simple for the "Color Alive" Launch Event in New York City.

20 of 20

2016

Jason LaVeris/Getty

Simpson rocked a sleek platinum 'do and bold eyeliner at the 24th annual Elton John AIDS Foundation Oscar viewing party in West Hollywood, Calif. 

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