Popsugar Celebrity Hilary Duff Hilary Duff Through the Years | Pictures Hilary Duff's Hollywood Evolution Proves She Has Always Been a Hollywood It Girl January 23, 2022 by Nick Maslow Image Source: Getty / Robert Mora Hilary Duff has had quite the Hollywood evolution. From her breakout role as a little witch in Casper Meets Wendy to her iconic Disney Channel role on Lizzie McGuire, the 34-year-old has been in the spotlight for most of her life, and she doesn't plan on stopping anytime soon. When she's not sharing sweet pictures of her son, Luca, Hilary is starring in Hulu's long-awaited How I Met Your Mother sequel series, How I Met Your Father. Over the years though, one thing has always remained: she's picture-perfect. See her transformation in her best pictures through the years. Related: 18 Times Hilary Duff Chased the Sun in a Bikini 1 2001 Image Source: Getty / Gregg DeGuire 1 / 38 2 2001 Image Source: Getty / Justin Kahn 2 / 38 3 2002 Image Source: Getty / SGranitz 3 / 38 4 2002 Image Source: Getty / L. Cohen 4 / 38 5 2003 Image Source: Getty / Djamilla Rosa Cochran 5 / 38 6 2003 Image Source: Getty / SGranitz 6 / 38 7 2004 Image Source: Getty / Scott Gries 7 / 38 8 2004 Image Source: Getty / Michael Caulfield Archive 8 / 38 9 2005 Image Source: Getty / Michael Loccisano 9 / 38 10 2005 Image Source: Getty / Evan Agostini 10 / 38 11 2006 Image Source: Getty / Djamilla Rosa Cochran 11 / 38 12 2006 Image Source: Getty / Frederick M. Brown 12 / 38 13 2007 Image Source: Getty / Jon Kopaloff 13 / 38 14 2007 Image Source: Getty / Scott Gries 14 / 38 15 2008 Image Source: Getty / Lisa Maree Williams 15 / 38 16 2008 Image Source: Getty / Mike Flokis 16 / 38 17 2009 Image Source: Getty / Ethan Miller 17 / 38 18 2009 Image Source: Getty / Michael Kovac 18 / 38 19 2010 Image Source: Getty / Charles Eshelman 19 / 38 20 2010 Image Source: Getty / Jason Merritt 20 / 38 21 2011 Image Source: Getty / Jesse Grant 21 / 38 22 2011 Image Source: Getty / Paul Archuleta 22 / 38 23 2012 Image Source: Getty / Jonathan Leibson 23 / 38 24 2012 Image Source: Getty / Steve Granitz 24 / 38 25 2013 Image Source: Getty / Frederick M. Brown 25 / 38 26 2013 Image Source: Getty / Christopher Polk 26 / 38 27 2014 Image Source: Getty / Allen Berezovsky 27 / 38 28 2014 Image Source: Getty / Jason LaVeris 28 / 38 29 2015 Image Source: Getty / Jim Spellman 29 / 38 30 2015 Image Source: Getty / Mike Pont 30 / 38 31 2016 Image Source: Getty / Theo Wargo 31 / 38 32 2016 Image Source: Getty / Tommaso Boddi 32 / 38 33 2017 Image Source: Getty / Robin Marchant 33 / 38 34 2017 Image Source: Getty / Ray Tamarra 34 / 38 35 2018 Image Source: Getty / Manny Carabel 35 / 38 36 2019 Image Source: Getty / Jon Kopaloff 36 / 38 37 2020 Image Source: Getty / Sarah Morris 37 / 38 38 2021 Image Source: Getty / Emma McIntyre 38 / 38 Hilary DuffNostalgiaRed CarpetCelebrity EvolutionsHaylie Duff