A variety of factors contribute to workers’ employment prospects, such as the levels of human and social capital that employees may possess. However, factors related to employers’ approaches to labor management contribute substantially to workers’ opportunities to find jobs that pay above poverty wages. This investigation examines mechanisms that may act to unevenly distribute opportunities for older workers to obtain higher-quality employment both across and within different retail firms. Specifically, this study considers the role of six Chicago-area department store retailers’ business strategies, and the associated brand images and hiring practices they use, as mechanisms that may limit or enhance employment opportunities available to workers age 50 and over. Because labor demand plays out on the front lines of organizations through the decisions managers make when hiring workers, managers’ perceptions of whether older workers may fit within the firm and within particular jobs may help explain the distribution of opportunities for older workers within and across department stores. As such, this study examines hiring managers’ perceptions of older workers and specifically the extent to which older workers are perceived as being a good fit for each firm and for particular jobs.