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This study examines the relationship between parenting styles and three psychological outcomes in adolescents: impostor phenomenon, self-esteem, and emotion dysregulation. Path analysis was used to test the mediating roles played by self-esteem and emotion dysregulation in the link between parenting and adolescents’ impostor feelings, distinguishing maternal and paternal effects and considering child gender. The sample included 220 adolescents who completed an online survey on parenting styles and psychological outcomes. Results indicated that maternal authoritative parenting directly reduced impostor feelings in males and indirectly (via self-esteem) in females. For fathers, self-esteem mediated this relationship only in males. Emotion dysregulation was linked to authoritarian parenting in adolescent females and permissive parenting in adolescent males, mediating the relationship between parenting styles and impostor feelings.