At present, individuals increasingly have to take ownership of their working lives. This situation requires them to self-manage and plan their careers. However, individuals' career management does not happen in a vacuum. Studies have therefore stressed the importance of organizations introducing Sustainable Human Resource Management to share the responsibility for individuals' employability. This is expected to motivate especially disadvantaged workers, such as older workers (≥ 50 years) and those working in lower-skilled jobs, to work longer across the life-span. In view of the growing scholarly and societal attention for Sustainable Career Development (SCD), the present study examines the relationships between workers' chronological age (comparing older workers with younger and middle-aged groups, respectively) and dimensions of self-reported employability, and how perceptions of negative (meta-)stereotyping regarding older workers' productivity, reliability, and personal adaptability moderate these relationships. To examine how possible underlying psychological mechanisms can affect individuals' labor market decisions and behaviors, we developed hypotheses derived from socio-emotional selectivity and self-categorization theory, which we tested using data collected among supermarket workers in various age groups (N = 98). Moderated regression analyses showed that, in line with our hypotheses, perceptions of negative age-based (meta-)stereotyping amplifies the negative effect of older workers' age on their self-perceived employability. In particular, we found that: (1) the older worker group reported lower levels of three of the distinguished employability dimensions (i.e., anticipation and optimization, corporate sense, and balance, but not occupational expertise and personal flexibility) and (2) perceptions of stronger negative (meta-)stereotypes regarding older workers in the organization had a moderating effect on the relationship between age group and four of the distinguished employability dimensions (i.e., occupational expertise, anticipation and optimization, corporate sense, and balance, but not personal flexibility). We conclude that age group membership as well as negative age-based (meta-)stereotypes deter older workers from enhancing their employability, which may potentially impact their career decisions and opportunities, especially in view of swift changing labor market demands. We argue, therefore, that Sustainable HR practices should focus on opposing negative age-based (meta-)stereotyping and on creating an inclusive work climate, meanwhile enhancing workers' ambitions and career opportunities over the life cycle.