Drawing from postmodern art theory this study explores the notions of representational politics and politics of representation in advertising. The paper begins with a review of key concepts of postmodern aesthetics and practices, and discusses various postmodern representational strategies identified as a result of a critical visual analysis of a controversial advertising campaign of the Italian clothing company Diesel. The paper concludes with a discussion of the problems and possibilities inherent in postmodern representation in advertising, the importance of critical literacy in the reception of such advertisements, and future research venues.