Anna with boyfriend Shelby Bryan and Rolling Stone co-founder Jann Wenner at Zac Posen, 2003.

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna Wintour

Anna at the CFDA Fashion Awards, 2003.

Anna at Kenneth Cole, 2003.

Anna at the Met Gala, 2003.

Anna Wintour at the Sean John Fall 2003 presentation in New York City.

It is a well-known fact that Vogue editor Anna Wintour spends the majority of her time aspiring to Lupita's flawlessness.* | Why "12 Years A Slave" Star Lupita Nyong'o Should Be Your New Fashion Idol

Anna Wintour

Anna

Founder and President of Jeffrey NY/Atlanta Jeffrey Kalinski and Editor-in-chief of American Vogue Anna Wintour attend Jeffrey Fashion Cares 2014 event at the 69th Regiment Armory in New York City.

Anna Wintour at The Royal Jewellers Garrard relaunch party in London, England.

Founder of Fashion Calendar Ruth Finley and editor-in-chief of American Vogue Anna Wintour attend the 2014 CFDA fashion awards at Alice Tully Hall, Lincoln Center.