This research explores the critical relationship between consumers, brands and the charity retail sector regarding garment care, repair and second-life ownership to encourage responsible wardrobe management. It acknowledges the importance of considered and active garment maintenance practices to ensure the longevity of a garment and retain value to prevent the purchasing of new, replacement garments. A qualitative methodology was informed by an extensive literature review, highlighting the identified problem space and creating a focus on critical gaps in knowledge. The core concepts of care and repair were explored through participatory workshops with charity retail sector volunteers and consumers to gain vital knowledge and skills in sustainable use behaviors. Collaborating with North-East based St. Oswald’s Hospice within the charity retail sector, the project empowers stakeholders to facilitate sustainable clothing behaviors intended to extend the lifetime of clothing. Key insights generated include the critical requirements of resource, skills and knowledge, and motivation to ensure holistic engagement with garment maintenance and care. Moreover, these factors need to be underpinned by an individual’s attachment of value to a garment, to rationalize the investment of time and effort in care and repair practices.