Fashion design entrepreneurs (FDEs) are compelled to embrace digitalisation to create a competitive advantage and provide the Web 2.0 (participative and social web) smart customer with the service they require. The purpose of this research was to determine how social media facilitates custom-made apparel design decisions in the FDE context. This study sets out to apply the third-generation activity theory to show the role social media plays in the activity system's result between a customer and FDE during the design process. Qualitative data from three independent exploratory studies conducted in Gauteng, South Africa, were used.