Among all Organisation for Economic Cooperation and Development countries, South Korean older adults work until the latest age. We investigate the extent to which work experiences over the life course and family circumstances can be associated with older workers' incentives to remain in the labor force beyond the statutory pension age. We explore gender-specific patterns of labor force exit and labor force re-entry in later life.Using panel data of South Korean older workers and retirees from 2006 to 2016, we estimate multilevel discrete-time models with random effects to predict their labor force transition process that unfolds over time.Results show that skilled manual workers are less likely to exit employment and more likely to re-enter the labor force. A longer history of self-employment is related to later retirement. The relationship between career characteristics and the risk of retirement is only significant for men. Late-aged employment transition among women appears to be more related to family conditions. Women who receive financial support from adult offspring are more likely to remain out of the labor force but this relationship is not pronounced among men.Policies aimed at extending working lives need to provide various types of social support to older job seekers, especially those who had low-class jobs and those without family networks.