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While the normative pattern of retirement is complete cessation of labor force activity, approximately one‐third of men work during their retirement. This research focuses on such “working‐retirees” by investigating the prevalence and patterns of occupational mobility from pre‐ to postretirement job, as well as the impact that institutional constraints on (re)employment in later life may have on the chances of occupational mobility. Using data from the older men's cohort of the National Longitudinal Surveys, a sample of working‐retirees was extracted from men who retired between 1967 and 1978. Results showed a substantial amount of occupational mobility among the working‐retired. The structure of mobility was found to be similar to younger labor force participants in that most mobility consists of moves to adjacent occupational categories. Unlike career mobility of nonretired workers, however, the large majority of moves constituted downward mobility. Using the economic segmentation perspective, log‐linear and logistic regression analyses indicated that working‐retirees whose preretirement jobs were in the core sector were more likely to experience occupational mobility. As a more specific indicator of bureaucratic control of the labor force, industry‐level pension coverage rates were used in the logistic regressions and higher rates of pension coverage were found to result in a greater likelihood of mobility. These results indicate that the considerable occupational mobility experienced by working‐retirees is partially the result of structural constraints on the employment of older men.