Adele
The Grammy winner scored her first cover in March 2012 (shot by Mert Alas and Marcus Piggott). Adele graced the pages of Vogue again in March 2016 (shot by Annie Leibovitz).
Jennifer Aniston
"America's Sweetheart" has modeled for the fashion magazine three times: in August 2002 (shot by Mario Testino), April 2006 (shot by Testino) and December 2008 (shot by Craig McDean).
Angelina Jolie
The Academy Award winner has been the face of Vogue five times. It began in April 2002 (shot by Leibovitz). Jolie later appeared on covers in March 2004 (shot by Testino), January 2007 (shot by Leibovitz), December 2010 (shot by Leibovitz) and November 2015 (shot by Leibovitz).
Michelle Obama
The First Lady trusted Leibovitz to shoot her in March 2009, April 2013 and December 2016.
Britney Spears
The singer played up her girl-next-door image in the November 2001 issue (shot by Herb Ritts).
Meryl Streep
In January 2012, at age 62, the Oscar-winning actress became the magazine's oldest cover star.