An upcycling practice involves working with remnants of material culture. It is about engaging with and responding to signs of wear. Interacting with traces of use—a smell, finger prints, imprints of a body that are left behind—this study documents and questions the experiences of working with clothing from a specific 1920s–30s historic archive belonging to a deceased female, and the way it informs and shapes the redesign of those garments. It is about understanding narratives behind the experiences of use. How does this affect the designer and their process? This study aims to enrich available knowledge of upcycling and upcyclers and their relationship to objects and attachment. In this article I will be reflecting on the first stage of my practice’s methodology, the reading of the piece; the initial engagement and interaction with the historic archive, which includes photographic documentation and exerpts from a reflective diary that records my material interactions whilst critically analysing and contextualising this process within fashion theory. My aim is to enrich the field of sustainable fashion by shedding light on a complex process that deals with death, memory, value, attachment, and history. By reflecting on my personal experiences with material, I will add to the discussion of designing with strategies that encourage sustainable design relationships; highlight and expand on existing theoretical discourse on textiles and mnemonic energy; and provide a deeper understanding of the practice of upcycling and the intimate materiality of wear. Upcycling fashion practices contribute a materiality perspective to anthropological processes of reading and understanding material culture.