In recent years, many studies are focusing on the best practices which make stores (both physical and virtual) more attractive, interesting and trustworthy for consumers [1]. The use of customized and efficient communication strategies addressed to specific consumers is an important topic of research [2] [3]. Furthermore, a growing interest has been put on the ways producers’ and retailers’ knowledge is used to add value to customers’ experiences [4]. While the use of new technological tools in online shops is often studied in academic research, the application of new technologies to the point of sales is a promising and relatively unexplored field of study. In particular the use of digital content and technologies allowing consumers to interact with products in new ways has been under-investigated by scholars and underestimated practitioners. For instance, many e-retailers already exploit the opportunities offered by interactive technologies, such as 3D virtual models, in order to enhance consumers shopping experience [5]. Their use in stores, however, is still limited. Hence, the development and use of new technologies supporting and influencing consumers during their shopping experience is a promising area of development for both academics and practitioners. Moreover, the study of digital technologies in web-based retail offers opportunities to single out approaches and practices useful also in traditional shops. Among the few existing applications there are shopping assistant systems based on shopping trolleys and handled devices [6]. Most of them use mobile and ubiquitous computing [7] [1]. Adding digital content to these tools can be a powerful means to influence customers’ experience. The aim is to support consumers, through a user-friendly interface, by giving them information related to products, promotions, new arrivals and so on. The main characteristics are the interactivity and the multimodality, which support an efficient, flexible and meaningful feeling of human-computer interaction [8] [9]. As a consequence, this powerful interaction is capable to influence consumer satisfaction, as well as the loyalty to retailers and the consumers’ buying behaviour [10]. In this scenario, it becomes very useful to understand how consumers’ and products/stores’ knowledge has to be managed and digitally represented. The study of online applications offers opportunities to investigate functioning tools based on the digital representation of consumers, products and stores’ knowledge. Besides, it is important to understand how this knowledge is capable to influence customers’ experience once converted into digital content. This special issue of the Journal of Digital Content Technology and its Applications was planned with the aim to publish researches regarding the fields of knowledge management and consumer behaviour in order to deeply understand the applications of new technologies in retailing and their impact on the design, development and modelling of consumers’ and products’ knowledge in order to improve consumers’ shopping experience and, as a consequence, influence their buying behaviour. Indeed, the overall goal was to encourage depth researches on digital contents management capable to support and affect consumer behaviour in different retail environments (both online and offline). A secondary purpose was to encourage consumer researches who might not usually consider the Journal of Digital Content Technology and its Applications as an alternative publication for their studies. The following mix of 6 papers emerged from the review process. We organized these manuscripts into two general categories: (1) consumers’, products’ and shops’ knowledge in online and offline retail and (2) impact of new technologies on consumers’ behaviour in the retail context. We are thankful to the editor of the Journal of Digital Content Technology and its Applications, for his encouragement and the initiation of the Special Issue. In addition, we are most appreciative of the many reviewers who supported in the revision process. Their work helped us to improve the quality of the papers and the development of this issue.