Digital disruption is not something that may happen in the future; it is currently happening and impacting all types of businesses, including retail. This chapter reflects cross-cultural similarities and differences. German and South African consumers increasingly use the internet to look for product information and to purchase online products and services. Nevertheless, about 25% of German and South African companies in the study sample are more or less offline, not offering even basic digital services, while a significant number of companies ignore opportunities for branding. The digital maturity and branding practices of 933 businesses located within the central business districts of two international cities of similar regional importance, namely Koblenz in Germany and Stellenbosch in South Africa, were investigated. Retailers were analysed in order to compare and contrast their progression along a digital maturity scale as well as their branding practices. The case study presented in this chapter aimed to provide a starting point for the development of such a picture.