Ashlee Simpson's Changing Looks

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

Ashlee Simpson's Changing Looks

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1 of 20

2001

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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

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

3 of 20

2004

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"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

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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

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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

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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

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

8 of 20

2006

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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

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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

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Simpson rocked piecey fringe and red hair in Vegas.

11 of 20

2008

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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

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

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13 of 20

2010

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Simpson rocked ombre locks for New York Fashion Week.

14 of 20

2010

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Simpson debuted a razored platinum pixie.

15 of 20

2011

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

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16 of 20

2012

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

17 of 20

2013

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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

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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

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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

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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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