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• • Ashlee Simpson at Katsuya Restaurant

    Ashlee Simpson in July of 2010 leaving Katsuya restaurant wearing a flowing black maxi dress. She looked very thin. Her... »

  • Ashlee Simpson in 2003

    Ashlee Simpson back in June of 2003 arriving with her sister, Jessica Simpson, for the MTV First Annual Bash in Hollywood.... »

  • Twisty Updo

    Ashlee Simpson in August of 2003 at the 5th Annual Family Television Awards which was held at the Beverly Hilton Hotel. She... »

  • Jet Black in 2010

    Ashlee Simpson-Wentz in January of 2010 in New York at the Hershy Store where she launches the New Additions to Pieces... »

  • Long, Blonde Ponytail

    Ashlee Simpson with Pete Wentz in 2007 at the Rolling Stone's 40th Anniversary Party.  Her long blonde ponytail hairstyle... »

  • Long, Red, Straight

    Before her concert at LAX Nightclub in Las Vegas in 2008. She looked hot with her long red straight hairstyle. Her long... »

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  2003 2004 2005 2007 2008 2010 adorable bangs black dress blonde braid braided brunette curly cute dark hair emo emo hairstyles eye makeup gold hoops hoop earrings hot Las Vegas LAX Nightclub layered long bangs long hairstyles medium length hairstyles middle part New Year's Eve nude lips open-back perfect Pete Wentz ponytail pretty Pure Nightclub red Rolling Stone's Party sexy side part teen hairstyles tousled up-do wavy