In this article, we discuss the experiential learnings from two collaborative research projects exploring the reuse of discarded competitive sails in Aotearoa New Zealand. The visually appealing and composite sail material, which normally goes to landfill because it is difficult to recycle, was the centre of our creative, practice-led and material-based approach, driven by sustainability and reflexivity. To achieve this, we applied environmental, social and economic lenses to our research processes and outcomes. We used two distinct projects as test cases to analyse and reflect on the realities, challenges, limitations and opportunities in the reuse of waste material in object and fashion design, also considering the differences between commercial design contexts and art-based approaches. In the first project, we aimed for replicable and commercial outcomes, emphasising material efficiency while simultaneously seeking to collaborate with and economically benefit a women-led refugee trust. In the second project, we aimed to create consciousness of the potential uses for discarded material, highlighting the visual aesthetics of the high-tech and historically meaningful sails in the context of Aotearoa New Zealand. We found that, while there were only minor differences in the design process, external conditions like funding agendas and exhibition spaces play an important role in the perception of design outcomes. Furthermore, there are structural barriers to addressing the social dimension of sustainability in commercial projects with not-for-profits, especially in short-term projects.