Many countries have implemented policies to extend working lives in response to population ageing, yet there remains little understanding of what drives paid work in later life, nor how this is changing over time. This paper utilises the 1988/89 Survey of Retirement and Retirement Plans, the 1999 British Household Panel Survey and the 2008 English Longitudinal Study of Ageing, to investigate drivers of paid work in the ten years surrounding state pension age (SPA) for women and men in, comparing cohorts born in the 1920s, 1930s and 1940s. Using optimal matching analysis with logistic and multinomial regression models, the study assesses the relative importance of lifecourse histories, socio-economic circumstances and contemporaneous factors, in determining paid work in mid- and later life. Participation in paid work in the five years preceding and beyond SPA increased markedly for men and women across cohorts, with women's lifecourses and engagement with paid work changing considerably in these periods. However, for women, a lifetime history of paid work remained a crucially important predictor of paid work in later life, and this relationship has strengthened over time. Experiencing divorce has also become an important driver of paid work around SPA for the youngest cohort. Having children later, and still having a mortgage, also independently predict labour force participation for women and men. Across all cohorts and for women and men, working at these older ages was a function of higher income and better health. These findings suggest that policies which enable people to maintain ties to paid work across the lifecourse may be more effective at encouraging later-life employment than those concerned only with postponing the retirement transition.