The honor goes to Lauren Hutton, who has graced the cover of the fashion magazine 26 times! With her short stature (5'7") and gap-toothed smile, some would consider her an atypical choice. However, for the editors of Vogue, her beauty transcends.
One of her most famous covers is from 1973, when she was shot by famed photographer Richard Avedon. You can see it here. Models Jean Shrimpton and Karen Graham were tied for second with 20 covers a piece, followed by Cindy Crawford. See who made the top 10, below (unfortunately, we couldn't find a photo of Graham, but you can see one of her covers here).