Representation of female and minority physicians varies across specialties and may influence career selection by medical students. To investigate the effect of demographic concordance between medical students and clinical role models on specialty selection, we conducted a survey of graduating medical students to assess the perceived importance and influence of third-year clerkship experiences with demographically concordant preceptors on their choice of specialty for post-graduate training. An 11-question survey was shared nationally through AAMC Organizational Student Representatives to medical students in the Class of 2023. Information gathered included demographics; specialty of choice; extent of exposure to preceptors of the same gender, race, or ethnicity during clinical clerkships; and perceived importance and influence of those interactions (Likert 1-5, Low-High) on specialty selection. A total of 84 students responded. Female students ascribed more importance to gender concordance with preceptors on the third-year clerkship most associated with their specialty of choice than males [3.4 (SD 1.2) vs. 1.3 (SD 0.8) respectively, p < 0.0001] and greater influence to gender concordance on final specialty selection [2.37 (SD 1.1) vs. 1.31 (SD 0.8) respectively, p < 0.0001]. Non-Caucasians ascribed more importance to race/ethnicity concordance than Caucasians [2.8 (SD 1.4) vs. 1.2 (SD 0.5) respectively, p < 0.0001] and greater influence to race/ethnicity concordance on final specialty selection [2.0 (SD 1.3) vs. 1.1 (SD 0.4) respectively, p < 0.0001]. Caucasian females ascribed the greatest importance to gender concordance (p < 0.001), non-Caucasian females ascribed the greatest influence of gender concordance (p < 0.001), and non-Caucasian females ascribed both the greatest importance (p < 0.001) and influence (p < 0.001) to race/ethnicity concordance. We found that gender and race/ethnicity concordance between students and clinical preceptors during third year clerkships is perceived as especially important and influential in specialty selection by minority and female medical students. These findings highlight the importance of diversity in gender and race/ethnicity representation by preceptors on clinical clerkships. The online version contains supplementary material available at 10.1007/s40670-024-02044-6.