It has been argued that lifecourse transitions are transformative moments for individuals when lifestyles, habits and behaviours are potentially open to contemplation and change. Within sustainability research such ‘moments of change’ are regarded as offering potential to encourage less environmentally damaging consumption patterns. Research on consumption indicates that orientations to material goods and their affective significance are complex. Whilst sociological work understands attachment to things as integral to maintaining kinship relations, this is hard to reconcile with long-standing moral concerns about materialism and psychological research which indicates a negative relationship between the acquisition of material objects and wellbeing, and the environmental implications of acquiring and divesting ‘stuff’. Yet there has been little engagement with how older people orient to their material possessions and divestment, the implications of this for later-life wellbeing and for environmental sustainability. In this paper, we draw these different strands of work together to understand how retirees relate to their material possessions and their divestment. Drawing on serial interviews with individuals in the United Kingdom, we explore how the transition to retirement highlights the complexity of participants’ attachment to things. While some items had profound relational significance, others were experienced as troublesome. Decisions on what to divest were shaped by pragmatic considerations and levels of attachment, whilst modes of divestment were aligned with values of thrift.