Gender is an undeniably significant element of human identity, contributing to multiple aspects of development. Previous research suggests that gender typicality, a sense that one is typical for one's own gender category, is associated with positive developmental outcomes among children while a sense of gender atypicality is generally associated with negative outcomes, including lowered self-esteem (Egan & Perry, 2001). This study further investigates the relationship between gender typicality and self-esteem from a developmental-contextual perspective by examining the relationship in the context of various developmental systems (e.g., school, peer group). Positive connections to developmental systems such as peers and school have been found to foster resilience by reinforcing strengths and buffering students from negative outcomes (Masten & Coatsworth, 1998). Therefore, it was hypothesized that classroom social support and school belonging would moderate the relationship between gender typicality and self-esteem by protecting gender atypical children from the negative cost of low self-esteem. Within the current sample, the relationship between gender typicality and self-esteem was more robust than in previous studies. While the moderating hypotheses were not confirmed, gender typicality was found to mediate the relationship between school belonging and self-esteem. The current findings underscore the vital role of gender and gender typicality in children's lives. Implications for prevention and intervention efforts in schools are discussed.