In an age of ever-increasing global interconnectedness within the fashion industry, this thesis paper explores the sukajan — more popularly known as the souvenir jacket — as an object of rich and, at times, contradictory transnational cultural exchange between the United States and Japan after the second world war. Using images from Japanese newspapers, fashion magazines, and documentary photographers in the postwar period to engage in visual and historical analysis, this project first grounds the origins of the sukajan within the cultural climate of the American Occupation of Japan. Through visual analysis of the sukajan in both Japanese and American film, this project then demonstrates how the jacket became interwoven with narratives of criminality, rebellion, and coolness on a global level. Finally, online fashion media analysis is utilized to trace the sukajan’s shifting stylistic and symbolic iterations and demonstrate how, through the process of mediatization, the sukajan moved from a symbol of subversive subcultural dress practices to a mainstream 21st fashion trend. Largely unexplored within the field of fashion studies, the sukajan is ultimately positioned by this project as a culturally hybridized garment featuring a fusion of both Eastern and Western aesthetics, techniques, and imaginations.