Most remembered for his portraits of Marilyn Monroe and James Dean, photographer Phil Stern’s subject matter ranged from the warfront to Hollywood. The year of the Dean’s premature death, Stern photographed the actor peeking out of his sweater, perhaps suggesting Dean’s enigmatic persona. In The New York Times T Magazine Style Men’s Fall Fashion 2013 issue, photographer and Saint Laurent designer Hedi Slimane photographed Justin Timberlake, similarly emerging from his sweater for a glimpse of the outside word.

Comparison Courtesy of Juan Andrés Puertas