Transparency within the supply chain has become a key priority for textile brands in response to the growing stakeholder concerns around social and environmental impacts of the textile value chain. Textile industry is extremely labour dependent and adds massively to the environmental degradation, adding on to this the highly complex and scattered global supply chain network makes it more difficult for brands to implement transparency in their supply base. Due to the low-cost labour in developing countries, the majority of the textile suppliers is located in South Asia, where the cultural values have been found to be in sharp contrast to the Global West. Many prior studies have also highlighted the lack of supplier’s top management support as the linking barrier to sustainable initiatives. Hence, this research was designed to investigate the behaviour and attitude of top management executives towards various transparency dimensions, i.e., Traceability, Sustainability conditions (Social and environmental) and Purchasing practices, in order to understand the underlying behavioural barriers. The semi-structured interview with 9 top management executives across India and Sri Lanka revealed three major themes: (a) Transparency as business imperative, (b) Distrustful relationship with brand and (c) Tendency to externalise responsibility. The Schwartz theory of cultural orientation was used to examine the role of cultural value in explaining the identified behaviour of top management executives.