The current study examines the relative impact of vocational interests and prestige on medical students’ aspired work environments. The following areas were included: family doctor, specialist in a private practice, specialist in a hospital, scientific researcher, and dentist. We also added the category “undecided students.” The sample consisted of 788 medical students in their preclinical years. Multinomial logistic regression analysis showed that the impact of vocational interests and prestige varied as a function of the medical students’ aspired work environments. Students with investigative interests particularly aspired to become scientific researchers (compared to the reference category of family doctor), whereas students interested in prestigious careers aspired to become specialists in a private practice (but not specialists in a hospital). Students with realistic interests particularly aspired to become dentists or specialists in a hospital. This article is concluded by a discussion of the impact of the person–environment fit on students’ career decisions.