Expectations regarding gendered behaviors are understood to emanate from many sources, including parents, peers, and the self but there has been little research directly comparing these three sources of pressure. The present study assessed felt pressure regarding masculine and feminine stereotypic behaviors and compared pressure from parents, peers, and the self and how these sources are associated with self-perceived gender typicality. Participants (N = 275; 53.09% female; grade 7 M = 12.35 years; grade 9 M = 14.3 years; 71% Anglo-Celtic) were recruited from independent schools in Sydney. Felt pressure from the self to engage in masculine behavior was greater than felt pressure from parents or peers. Male adolescents reported higher felt pressure to conform to gender conforming behavior from parents and the self and pressure to avoid gender nonconforming behavior was greatest from peers. Female adolescents reported felt pressure to conform to gender nonconforming behaviors and this pressure was the strongest from the self. Additionally, for both genders, felt pressure from the self was most consistently associated with gender typicality. These findings highlight the importance of self-expectations for gender cognitions relating to both masculine and feminine behaviors.