Purpose To investigate the difference in character strengths (CSs) between patients with and without polycystic ovary syndrome (PCOS) and the association between biological (i.e., testosterone levels) and psychological factors (i.e., character strengths). Patients and methods A total of 99 women divided into PCOS (49) and non-PCOS (50) groups who presented to the gynecological clinics at the women’s center in the American University of Beirut Medical Center in 2017 were included. Women were assessed for testosterone bioavailable levels and completed a questionnaire that included Hospital Anxiety and Depression Scale and Values in Action Survey-72. Univariate and multivariable analyses were performed to examine the association of CSs between the two groups and its predictors. Results The scores of hope, judgement, perspective, and transcendence of the PCOS group were significantly higher in comparison with healthy participants. An increase in free androgen index was negatively correlated to the score of judgement only. Conclusion Women with PCOS have their own profile of character strengths and virtues that constitute judgement, hope, perspective, and transcendence. This in turn can be utilized to reinforce those personality strengths and thus decrease the psychological distress and mood disorders accompanied with this disease.