The article deals with reading of Walter Benjamin’s works focused on new media. The article puts specific emphasis on the notions of ‘aura’ and ‘flaneur,’ two well-known themes in Benjamin´s scholarship. The article argues for the inseparability of old and new, modern and postmodern theory of media and illustrates their close connections in Benjamin’s texts. The author presents a sceptical view of the idea that the advent of digital new media is connected by necessity to a major historical break. He concludes that Benjamin’s theory of new media is highly useful for describing and understanding the current new media communication and subjectivity.