How are the work trajectories of Chilean women? This qualitative study analyzes the female work trajectories through interviews and biograms in a sample of 50 Chilean women, professionals and non-professionals, between the ages of 24 and 88. The article proposes an original typology of female work trajectories and relates type of work trajectory with Piore’s theory of labor market segmentation. The paper discusses the challenges and weaknesses of the Chilean women’s labor outcome and presents recent data to extrapolate the impact of the COVID-19 pandemic on vulnerable work trajectories. It considers the type of State and possible actions to achieve greater welfare and social development regarding gender equality.