In the midst of the second wave of feminism, famed Esquire Art Director George Lois questioned gender roles, playfully conjuring up the vision of a beautiful woman, lathered up in shaving cream, razor in hand. Photographer Jean-Paul Goude was appointed to execute Lois’s vision, starring the Italian Actress Virna Lisi. Commonly misidentified as Marilyn Monroe, despite the fact that Monroe had passed three years earlier, Lisi was reportedly instantly onboard with the project despite its unflattering nature–Hitchcock blond Kim Novak’s publicist is said to have hung up on Lois after hearing his proposed cover. To celebrate the 75th Anniversary of the magazine, Esquire would look to their June 1965 issue, photographing a similarly coiffed Jessica Simpson mid-shave for the May 2008 issue.