Referred to as the 'Golden Dustman' (Evans 1998) Martin Margiela's approach to sourcing and reworking vintage garments was likened to that of a Victorian ragpicker. Today, the abundance of second hand clothing donated to charity shops presents fashion designers with the opportunity to reprise Margiela's role, by considering textile waste as valuable, raw materials. Donating unwanted garments to charity is a prolific cultural practice, perceived as philanthropic and sustainable. However, donations of unwanted clothing comprise 80% fast fashion, which cannot easily be re-used, re-sold or biodegraded. Emmanuel House, a homeless charity in Nottingham have a three-tier sorting system: 1. To clothe its service users; 2. for re-sale in the charity’s shop to fund its work; 3. to be sold as 'rag' by the kilo (shipped to 3rd world countries). This conversion to cash process raises various ethical concerns. This paper reports on a social/design innovation collaboration between Emmanuel House, and Year One BA Fashion Design students, which is raising awareness of what happens to clothing donated to charities, including: the resource rich sorting process; unwanted clothing versus clothing poverty; the potential for a circular design approach at end of product lifetime; how strategic re-design can lead to innovative, suitable clothes that enhance user experience and self-esteem. Through volunteering for Emmanuel House, the students have acquired insights into homelessness and sorting charitable donations. By using their tacit knowledge of textile quality and performance, garment construction, fit and silhouette, they have identified valuable materials within existing garments. The selected items formed the basis for critically designed solutions, created using a 'deconstruction/ reconstruction' methodology, incorporating upcycling, customization, overdyeing and repair. Outcomes integrate practical details to accommodate rough sleeping and outdoor, nomadic living, including: waterproof/warm outerwear; multifunctionality/ transformability; multiple pockets for carrying/concealing items; e-textile functionality to augment light/ heat