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. The study participants for each study were purposefully selected, either as customers of custom-made apparel designers or custom-made apparel designers of SMEs. Content analysis of social media-related extracts from transcribed data was used to identify the technological and semiotic elements of the mediating activities within the customer (subject) and designer (subject) activity systems. Findings suggest that social media as technology, for both activity systems, acts as an inspirational, marketing, distance bridging and design-process tool through the semiotic use of messaging and pictures. Through social media technology, comments and pictures facilitate the semiotic use of social media in each of these tools. Between the two activity systems, the design process facilitates the introduction, design development, or agreement and design progress or completion phases of the process, using comments and pictures as semiotic elements of communication. Through mobile phones, design communication between the activity systems is supported within the fashion community considering social media policy and regulations. Social media is a valuable tool through which the customer and FDE can engage in the design process in an emerging context. The success of the FDE may be reliant on the use of social media and better advocacy of the entrepreneurial business context within design education. FDEs need to understand the importance of the dialectics between creative design and creative business management to ensure the future of fashion designers in an emerging context such as South Africa.