During recent decades, labour market participation among older workers in the Netherlands has increased significantly. Postponing workers’ labour market withdrawal potentially makes their retirement patterns more uncertain and less predictable. This article uses Dutch register data to analyse de-standardisation and differentiation of retirement trajectories of men and women born between 1940 and 1946 for the age bracket of 59–65 (N = 12,843). The results indicate that retirement trajectories of men have become more homogeneous, whereas those of women somewhat more heterogeneous. Simultaneously, retirement patterns of both men and women became more complex from one birth year to another.