Dean Martin is seen "circa 1960s," according to the original caption to this photo, which could really mean anything from 1958 to 1972. We're going to guess 1960, the year that he made the film Ocean's Eleven with his pals Frank Sinatra and Sammy Davis, Jr. In fact, in that movie he wears a jacket that looks just like this one. (Check the scene around the pool table where he tries to talk the others out of their robbery plan.) So that's it: we're definitely going with 1960.