Adapting a circular system through business model experimentation can generate profit and sustainable growth for fashion firms. Business model experimentation explores novel opportunities to be at the forefront of transforming existing markets. Remanufacturing is one circular strategy that entails the process of recovering both raw material and value from end-of-life products for the production of new items. Remanufacturing in the context of business model experimentation is a promising solution in the fashion and textile industry to drive the transition into a circular economy. Through case study research the phenomenon of remanufacturing business model experimentation within the fashion and textile industry is investigated. The case phenomenon is investigated by means of the Re:workwear project, in which the brand Cheap Monday uses discarded workwear for a remanufactured collection next to its common collection. The focus of the study is on remanufacturing business model experimentation alongside the brand’s business-as-usual and decisive factors of this phenomenon. The processes and -steps within experimentation were analysed through semi-structured interviews with various involved parties of the supply chain. A framework combining the Business Model Canvas and the stepwise approach of business model experimentation by Bocken et al. (2017) is developed and applied throughout the research. It is found that (1) motivation and scope, (2) input material, (3) flexibility, (4) stakeholder collaboration and (5) system development are decisive factors for remanufacturing business model experimentation. Further research is necessary to investigate the phenomenon in other settings and within a variety of other firms in the industry in order to test the findings and validate the generalisability.