Since 2011, the authors have been developing creative and playful sustainable design workshop tools to understand, develop and share knowledge and ideas with other designers. These tools originated through practice-led research methods, involving prototyping, to explore and consolidate research theories. By translating design strategies into both realised artefacts and tools for engaging others through design, the authors have continuously transformed practice and theory in the field. More recently the theory has become focused on the starting point of ‘circular models for design’, in particular, designing for lifecycle speeds. This paper discusses some of the tools used for exploring ‘product longevity’ and ‘circular’, resulting in further insights for future design, including the current understanding of ‘longevity’ as both a product and a material consideration, with two seemingly opposed strategies. The authors research groups' primary methodological approach is through designing and making textile/fashion artifacts to generate new theory; in order to share this approach and support others outside of the group to use making as a key research method they often design and facilitate workshops and create tools, which are then shared via the project website. In this paper tools developed specifically to design to extend the life of a fashion textile product are discussed and the creative outcomes generated are presented. The playful tools generated playful ideas and by reflecting via field notes on these industry workshop outputs the authors here offer a set of tools to support designing sustainable and circular textiles for long life.