The positive relationship between self-perceived gender typicality and self-esteem has previously been found in several studies with adolescents and adults. But what about cross-cultural differences? It was hypothesized that the relationship would partially depend on the extent of gender equality and prevailing sexist attitudes in a country. In the present study, 2377 participants from nine nations with a gradually decreasing Global Gender Gap Index (GGI) provided online ratings of the Adult Gender Typicality Scale (AGT), the Bem Sex Role Inventory (BSRI), the Rosenberg Self-Esteem Scale (RSES), and the Ambivalent Sexism Inventory (ASI). A significant, positive correlation between gender typicality and self-esteem was present in both men and women across the whole sample. Only in the male sample, the relationship lessened significantly with increasing levels of gender equality (r = -.77). However, in the female sample, agreement with benevolent sexism a seemingly positive form of sexism that subtly underlines womens subordinate status enhanced the relationship between gender typicality and self-esteem significantly.