The processes of technological innovation have been widely researched, but their interactions with another type of innovation that is particularly important in sectors like the fashion and the media content industries have been neglected: stylistic innovation. This paper puts forward the idea that a better understanding of such interactions between content and technology in the media industries might help explaining differences in the receptiveness of firms towards new technological opportunities. The nature of the interactions, so it is argued in this paper, depends on three groups of key factors at the level of the product, the organization and the industry: among them, first, the locations of the different types of innovation in the media product's components; second, organizational factors like the identity and the reputation of a firm with respect to the above types of innovation; and third, the industry-specific characteristics of the certification environment in which the firms operate. Awards are discussed as specific instantiations of micro certification environments indicating quality with respect to stylistic and/or technological product features. To round off the theoretical part, a definition of stylistic innovation is developed with reference to the key concepts discussed in this paper. Within the media sector the literary publishing industry has been chosen to provide the subject of the empirical part. Two cases related to the introduction of eBook technology are presented: one is a study of the first digital literary publisher in Europe and the other is a case study of the first international eBook award, which mixes technological and stylistic criteria. Theory and cases lead to a number of hypotheses offered as potential departure points for future research into the interactions between innovation in style and technology.