The proportion of individuals extending their working lives beyond full pension age (FPA) has increased considerably over the last twenty years worldwide. Most research on the extension of working lives has examined what determines whether older people remain attached to the labor market, neglecting the diversity of their labor force statuses. Also, what we know from this line of inquiry is derived almost exclusively from developed countries, leaving other regions, such as Latin America, unexplored. Based on a life-course approach, we close these research gaps by analyzing how types of lifetime employment and coresidential trajectories determine both the extension of working lives beyond FPA and the diverse labor force statuses of older workers in Chile. We draw on a rich and comprehensive life history dataset of a cohort of Chileans currently aged 65–75 and use longitudinal and cross-sectional statistical methods. Our results indicate that individuals who followed diverse employment trajectories throughout their lives (whether in formal or informal jobs) but permanently coresided with a partner and adult children were most likely to be partly retired in old age (i.e., working while receiving a pension). Those who followed more informal employment trajectories while living permanently with a partner were more likely to remain active, particularly through self-employment, beyond FPA. We stress the importance for future labor policies aimed at older populations to consider the diversity of life-course trajectories in the employment and family domains.