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Ashlee Simpson Then & Now! The Many Looks of This Celebrity Mom (Photos)

Blonde, brunette, black and blonde again. Grunge, girly and all in leather.  New nose, old nose. Ashlee Simpson has had many many looks over her time in the spotlight.  When we first met Ashlee almost ten years ago, she went from the girl next door, to a femme fatale, to a married lady to a mom. And her style has changed throughout it all.

And now Ashlee is setting upon a new adventure as a single mom who is co-parenting with her ex- Pete Wentz. And her new chapter includes a new man! She has been reportedly been seen smooching with actor Vincent Piazza, who plays gangster Lucky Luciano on HBO’s Boardwalk Empire.

Will she get yet another new look? Check out this slideshow of a dozen of her old looks. Do you have a favorite? One you’d like to see again?

nggallery id=’114905′

  • Ashlee Simpson 1 of 13
    Ashlee Simpson
    01/16/2008 - Ashlee Simpson - "Cloverfield" Los Angeles Premiere
  • Ashlee Simpson 2 of 13
    Ashlee Simpson
    09/07/2008 - Ashlee Simpson - 2008 MTV Video Music Awards -
  • Ashlee Simpson 3 of 13
    Ashlee Simpson
    11/02/2010 - Ashlee Simpson
  • Ashlee Simpson 4 of 13
    Ashlee Simpson
    Broadway's "Chicago'" 10th Anniversary Ambassador Theatre, NYC 14/11/06
  • Ashlee Simpson 5 of 13
    Ashlee Simpson
    09/07/2007 - Ashlee Simpson -
  • Ashlee Simpson 6 of 13
    Ashlee Simpson
    06/24/2009 - Ashlee Simpson - Axe Instinct and Rolling Stone Magazine Present "The Power of Leather" Party
  • Ashlee Simpson-Wentz 7 of 13
    Ashlee Simpson-Wentz
    01/27/2010 - Ashlee Simpson
  • Ashlee Simpson 8 of 13
    Ashlee Simpson
    08/02/2003 - Ashlee Simpson - 2003
  • Ashlee Simpson 9 of 13
    Ashlee Simpson
    08/08/2004 - Ashlee Simpson - 2004 Teen Choice Awards
  • Ashlee Simpson 10 of 13
    Ashlee Simpson
    12/02/2002 - Ashlee Simpson - "The Hot Chick" Hollywood Premiere
  • Ashlee Simpson-Wentz 11 of 13
    Ashlee Simpson-Wentz
    10/03/2009 - Ashlee Simpson
  • Ashlee Simpson 12 of 13
    Ashlee Simpson
    08/13/2010 - Ashlee Simpson
  • Ashlee Simpson-Wentz 13 of 13
    Ashlee Simpson-Wentz
    09/14/2009 - Ashlee Simpson-Wentz
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