Despite starring in only three films in his career, James Dean remains a street style icon. This paper holds that Dean’s style was one of the first and greatest inspirations for modern streetwear designs. SportingLee 101 Riders with a white tee and work boots as well as the iconic, red blouson jacket in Rebel Without a Cause (Ray, 1955), he and costumer Moss Mabry changed fashion forever with a sense of style that is timeless. For the first time dressing down was suddenly more favorable than dressing up. This paper will look at how fashion and pop culture capitalized on the movie’s look.