Making a comeback this season is the Penny loafer. Following the eagerly anticipated film, The Wolf on Wall Street, Leonardo DiCaprio plays Jordan Belfort who sports this classic style throughout the film. The Penny loafer originated in the 1930’s and gets its name from the times when school children would keep an emergency penny in their shoes for use in payphones. It’s population grew when celebrities such as, James Dean, JFK and Michael Jackson were seen wearing the style. Chose from the Exeter, Broadway or Russel from Herring Shoes…