Retirement has traditionally been seen as the beginning of old age. It has been depicted as mandatory expulsion from the workforce and seen to mark the transition to a period of ill health and poverty. Such ideas and associations are however being challenged in the developed world by socio-demographic changes in retirement and old age. People in the United Kingdom as elsewhere are living longer and healthier lives, and many older people have access to non-state incomes that afford them a reasonable standard of living in retirement. There is however still concern that inequalities persist into old age. Data from two waves of the British Whitehall II study have been used to assess the relative effects of occupational grade, psychological and general health during working life, and retirement patterns or pathways on activities, attitudes to health and income in retirement. The results show that the majority of the sample reported good health, financial security and overall satisfaction with life, but with observable inequalities. Regression analyses demonstrate that pre-retirement circumstances generally had a greater effect on later life than the retirement route or pathway. Retirement no longer represents a drastic break between working and post-work life but rather, the results suggest, there are continuities between the two periods. It is concluded that the main causes of inequalities in retirement are work-based rather than in retirement itself.