Background: Medical specialty is a critical choice in a physician's life because it determines their professional future and medical practice. While some are motivated to choose a specific specialty based on the monetary gain it can provide, others are inspired by seeing the work performed by a physician or by a patient's recovery. It is common to stereotype doctors' personalities by their specialty. Methods: This was a cross-sectional survey study in which we administered the 100-item HEXACO Personality Inventory-Revised to 292 medical students between September 2018 and March 2019. We evaluated six different domains of personality traits. We also included questions about their medical specialty of choice, their least preferred specialty, and the motivation behind these choices. The participants included 175 women (59.9%) and 117 men (40.1%). Results: When the participants were asked about their preferred type of medical specialty, 52.4% indicated a preference for surgical specialties (surgical group) vs 47.6% who preferred clinical specialties (clinical group). We found that the surgical group showed significantly higher scores for Extraversion and Organization domains, while the clinical group showed significantly higher scores on the Honesty-Humility, Emotionality, and Agreeableness domains. We identified critical differences within the overall group of medical students by their medical specialty preference. Conclusions: Some classical stereotypes were confirmed by our results, such as surgical specialists tending to be more extroverted and organized, whereas clinical specialists were prone to being more introverted, anxious, and more emotionally attached to their patients.