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 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | August | 1999 |  |  |  |  |  | Liv Tyler |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | January | 2000 | | | | | | Sarah Michelle Gellar |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | February | 2000 |  |  |  |  |  | Sarah Michelle Gellar |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | March | 2003 | | | | | | Christina Ricci |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | August | 2003 |  |  |  |  |  | Christina Aguilera |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | September | 2003 | | | | | | Michael Pitt |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | September | 2003 |  |  |  |  |  | Sarah Polley |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | October | 2003 | | | | | | Zooey Deschanel |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | November | 2003 |  |  |  |  |  | Chloe Sevigny |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | December | 2003 | | | | | | Mandy Moore |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | April | 2004 |  |  |  |  |  | Maria Carla |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | May | 2004 | | | | | | Maggie Gyllenhaal |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | July | 2004 |  |  |  |  |  | Avril Lavigne |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | September | 2004 | | | | | | Jessica Miller |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | August | 2006 |  |  |  |  |  | Ashley Olsen |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | September | 2006 | | | | | | Avril Lavigne |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | November | 2006 |  |  |  |  |  | Amber Tamblyn |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | January | 2007 | | | | | | Michelle Williams |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | February | 2007 |  |  |  |  |  | Sienna Miller |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | March | 2007 | | | | | | Christina Ricci |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | April | 2007 |  |  |  |  |  | Christina Aguilera |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | May | 2007 | | | | | | Lindsay Lohan |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | September | 2007 |  |  |  |  |  | Evan Rachel Wood |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | January | 2008 | | | | | | Mary Kate Olsen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | March | 2008 |  |  |  |  |  | Rachel Bilson |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | April | 2008 | | | | | | Chloe Sevigny,Anja Rubik,Clemence Poesy |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | May | 2008 |  |  |  |  |  | Leighton Meester |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | May | 2008 | | | | | | Blake Lively |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | July | 2008 |  |  |  |  |  | Scarlett Johansson |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | August | 2008 | | | | | | Mischa Barton |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | September | 2008 |  |  |  |  |  | Shenae Grimes,AnnaLynne McCord,Jessica Stroup |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | October | 2008 | | | | | | Zooey Deschanel |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | November | 2008 |  |  |  |  |  | Paris Hilton |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | January | 2009 | | | | | | Lily Allen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | February | 2009 |  |  |  |  |  | Camilla Belle |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | March | 2009 | | | | | | Kristen Stewart |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | April | 2009 |  |  |  |  |  | Lindsay Lohan |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | May | 2009 | | | | | | Kat Dennings,Olivia Thirlby |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | July | 2009 |  |  |  |  |  | Karen O |  |
| | | | | | | | |  | | | | | | | Nylon Magazine | | | | | | | August | 2009 | | | | | | Sienna Miller |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | Nylon Magazine |  |  |  |  |  |  | September | 2009 |  |  |  |  |  | Anna Paquin |  |