Abstract In order to capture the rapidly changing reality of older workers, it is important to study retirement not as a one-off transition, but rather as a series of diverse pathways that unfold during the period before and after reaching the full retirement age. The retirement transitions of men and women have been shown to vary widely according to individual characteristics such as health, education and marital status, but also according to macro-institutional factors, such as welfare regimes and gender norms. While there is a consensus about the combined influence of institutional and individual factors in shaping retirement transitions, previous research has rarely included both levels of analysis. This study aims to close this research gap. Using a pooled-country dataset from three panel surveys, covering 11 nations, we examine the retirement pathways of 1,594 women and 1,105 men during a 12-year period (2004–2016) around the country- and gender-specific full pension age. Results show that retirement pathways diverge considerably across countries and lifecourse regimes. The distribution of men and women between the different pathways is also variable, both within and across societal contexts. More importantly, the influence of individual-level characteristics, such as education, on the gendering of retirement pathways is not identical across societal contexts. These findings provide useful insights into the gender-differentiated implications of policies aimed at extending working lives.