Objectives: The role of personality in occupational specialty choices has been explored in many parts of the world. To our knowledge, there is a dearth of such studies in the Arab/Islamic population and Oman is no exception. This study aimed to explore the relationship between personality traits and specialty choice among residents of Oman Medical Specialty Board (OMSB). Methods: A cross-sectional study was carried out among Omani resident physicians working under OMSB. The Eysenck Personality Questionnaire–Revised was employed to quantify personality subtypes (e.g., psychoticism, extraversion, and neuroticism). Specialties were categorized as surgical, medical, and diagnostics as per standard of North American medical specialties. A total of 255 residents in 17 medical specialties participated in the study (m = 40.4%; f = 59.6%) of 300 eligible subjects giving a response rate of 85.0%. Results: Respondents who had chosen surgical specialties scored significantly higher on the psychoticism subscale than those who had opted for medical and diagnostic specialties. As for individual specialties, orthopedic respondents had statistically significant higher mean scores on psychoticism and neuroticism compared to radiologists and psychiatrists who scored the lowest in the two personality traits, respectively. Conclusions: This study found statistically significant associations between personality traits and choices of specialty by young Omani doctors. We recommend more detailed studies that examine further psychological and cultural variables that are likely to affect the choices of specializations by young Omani professionals in both medical and non-medical fields.