Retirement is frequently a period of change, when the roles and relationships associated with individuals' previous labour market positions are transformed. It is also a time when personal relationships, including the marital relationship and relationships with friends and family, come under increased scrutiny and may be realigned. Many studies of adjustment to retirement focus primarily on individual motivation; by contrast, this paper seeks to examine the structure of resources within which such decisions are framed. The paper examines the contribution that gender roles and identities make to the overall configuration of resources available to particular individuals. It draws upon qualitative research conducted with older people in four contrasting parts of the United Kingdom, and examines the combination of labour market and non-labour-market activities in which they are involved prior to state retirement age and as they withdraw from paid work. It explores how older people invoke various gendered identities to negotiate change and continuity during this time. The paper argues that gender roles and identities are central to this process and that the reflexive deployment of gender may rank alongside financial resources and social capital in its importance to the achievement of satisfying retirement transitions. Amongst those interviewed, traditional gendered roles predominated, and these sat less comfortably with retirement for men than for women.