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 | W |
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 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | October | 1995 |  |  |  |  |  | Claudia Schiffer |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | December | 1995 | | | | | | Kate Moss,Stella Tennant |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | January | 1996 |  |  |  |  |  | Christy Turlington |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | December | 1996 | | | | | | Kate Moss |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | April | 1998 |  |  |  |  |  | Amber Valletta |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | July | 1998 | | | | | | Liv Tyler |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | February | 1999 |  |  |  |  |  | Michelle Pfeiffer |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | May | 1999 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | June | 1999 |  |  |  |  |  | Cindy Crawford |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | July | 1999 | | | | | | Liv Tyler |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | August | 1999 |  |  |  |  |  | Bridget Hall |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | November | 1999 | | | | | | Jennifer Aniston |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | December | 1999 |  |  |  |  |  | Jodie Foster |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | January | 2000 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | February | 2000 |  |  |  |  |  | Gisele Bundchen |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | March | 2000 | | | | | | Christy Turlington |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | May | 2000 |  |  |  |  |  | Claudia Schiffer |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | June | 2000 | | | | | | Cindy Crawford |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | September | 2000 |  |  |  |  |  | Kate Moss |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | October | 2000 | | | | | | Stephanie Seymour |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | December | 2000 |  |  |  |  |  | Hilary Swank |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | March | 2001 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | July | 2001 |  |  |  |  |  | Christy Turlington |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | August | 2001 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | September | 2001 |  |  |  |  |  | Gwyneth Paltrow |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | October | 2001 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | December | 2001 |  |  |  |  |  | Renee Zellweger |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | February | 2002 | | | | | | Gisele Bundchen |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | April | 2002 |  |  |  |  |  | Lauren Bush,Hugh Grant |  |
| | | | | | | | |  | | | | | | | W Magazine | | | | | | | June | 2002 | | | | | | Winona Ryder |  |
 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | W Magazine |  |  |  |  |  |  | August | 2002 |  |  |  |  |  | Naomi Campbell,Natalia Vodianova,Kate Moss,Christy Turlington,Stephanie Seymour,Claudia Schiffer,Cindy Crawford,Gisele Bundchen,Iman,Shalom Harlow,Patti Hansen |  |