Discrepancy stress, stress about being perceived to not conform to one's gender role (i.e., gender role discrepancy), has demonstrated effects on risky sexual and violent behaviors. However, evidence of these effects has been limited to men and boys, neglecting the impact gender role discrepancy and discrepancy stress may have on girls. In addition, no study to date, has assessed the mental health correlates of gender role discrepancy and discrepancy stress. In the current study, we sought to elucidate the relationship between perceived feminine discrepancy and feminine discrepancy stress and psychosocial maladjustment while controlling for trauma symptoms stemming from the potential repercussions of feminine discrepancy. Maladjustment was measured by creating a second-order latent factor derived from four first-order latent constructs: sexual behavior, substance use, mood disorder symptoms, and hopelessness. Data are drawn from a cross-sectional sample of female students in middle and high school (N = 643) who completed self-report questionnaires. Using structural equation modeling, we found girls reporting feminine discrepancy (i.e., less feminine than the average girl) were more likely to report feminine discrepancy stress and trauma symptomatology. Controlling for feminine discrepancy and trauma symptoms, the relationship between discrepancy stress and maladjustment was positive and significant. Additionally, girls reporting feminine discrepancy scored higher on trauma symptomatology, and trauma demonstrated a strong direct effect on psychosocial maladjustment. These data suggest that developing trauma focused prevention strategies that incorporate social norms around gender socialization may have an impact on multiple behavioral and mental health problems.