This exploratory work investigates the burgeoning integration of ‘cradle to cradle’ practices into primary strategic activities of procurement, production and sales by ten London based fashion businesses, analysing how profits are derived from offsetting the high costs of sustainable inputs against savings from innovative strategic choices in the production value chain. This research was influenced by the background knowledge that in the global fashion industry, less than 1 per cent of the recycled textiles are converted into new wearable materials, and even more of these textiles end up in landfills. However, this unsustainable tradition in the fashion industry may gradually give way to a mainstream circular economic best practice in the fashion industry, even as the Mckinsey Report found that sustainability will be a significant factor for consumer purchasing mass market apparels by 2025. Based on the semi-structured interview of the ten fashion business owners and the analyses of internal strategic policy documents including budgets, we adopted Garret Hardin’s ‘Tragedy of the Commons’ and Ulrich Beck’s risk society as the lens view through which the qualitative data derived from these fashion businesses were discussed in order to bring out the illustrative extracts and sub-themes. Through the application of interpretive methodological approach, we were able to generate the themes suggesting the ‘Becksian’ reflexive modernization and dis-embedding mechanisms in analysing the issue of trust in luxury fashion environment. We were able to demonstrate the multidisciplinary and multifaceted nature of the use of modern technology in achieving a closed-loop circular economy in luxury fashion business(es) and its interconnectedness within the concentric layers of the value-chain, which is part of the economy, which is in turn a subset of the society and the environment. As businesses are expected to adapt their strategies to the changing environment, we argue that dematerialization in fashion is still at its infancy, and some deliberate actions on the part of economic policy-makers may be required in due course as this is connected to social sustainability amongst others. This article contributes new empirical data to the understanding of luxury fashion business in a circular economy, which is a departure from the linear economy with its attendant externalities. The adoption of a sustainable fashion business model may be pivotal to combating the inefficiency costs built into the fashion industry, and if successful, may be replicated in other jurisdictions in due course.