The prevalence of polycystic ovary syndrome (PCOS) among trans men has been reported as higher than among the cisgender population, which varies between 14.4% and 58%. In this cross-sectional study, we aimed to evaluate the association of oligo-anovulation and/or features of hyperandrogenism with the scores on the Utrecht Gender Dysphoria Scale (UGDS), the Body Image Scale (BIS), and the Short Form-36 Health Survey (SF-36) in treatment-naive trans men with PCOS seeking help for gender transition. The study sample consisted of trans men who were diagnosed with gender dysphoria (GD) between December 2019 and November 2020. To assess body dissatisfaction and psychological functioning, the UGDS, BIS, and SF-36 were administered to all transgender individuals as part of the routine assessment procedure. A total of 49 treatment-naive trans men were included in our study; 38.8% (n = 19) of the participants were diagnosed with PCOS using the Rotterdam 2003 criteria. The scores of UGDS and BIS were significantly lower in the PCOS group compared with the non-PCOS group ( p < 0.001 and p = 0.003, respectively). Among the eight parameters within SF-36, general health, emotional role, and vitality scores were significantly higher in the PCOS group ( p = 0.031, p = 0.015, and p = 0.006, respectively). Our study is the first study that demonstrates significantly lower GD, higher body image satisfaction and quality of life in trans men with PCOS compared with those without PCOS. Our findings are promising for larger prospective cohort studies to develop a consensus on the management of PCOS in trans men.