In this study, it was hypothesized that (1) four categories of retail career socialization (i.e., socialization related to education, work, retail establishments, and family) will predict three aspects of retail career preference (i.e., intrinsic, extrinsic, and lifestyle) and (2) retail career preference will, in turn, predict retail career choice. College juniors and seniors nationwide (N = 723) responded to a survey questionnaire. The findings indicated that socialization related to retail work and education had direct and indirect effects on retail career choice. Retail shopping–related socialization had pervasive, indirect effects on retail career choice via all three components of retail career preference. Family-related socialization had an overall negligible indirect effect on retail career choice through retail career preference. The intrinsic enjoyment component of retail career preference had the greatest effect on retail career choice, followed by the extrinsic compensation and lifestyle flexibility components of retail career preference.