This article investigates early childhood educators’ perceptions of children’s gender-role play and the impact their cultural background plays in their gender identity and play behaviors. Through qualitative in-depth interviews, early childhood educators in Canada (n = 40) were asked questions relating to their experiences with children from various cultural backgrounds, how cultural diversity impacted a child’s gender identification, and who early childhood educators felt struggled more with gender identity. In general, respondents felt that cultural background could have an impact of gender identification, and that while boys and girls both struggle with gender identity, girls had the added stress of competing with popular culture expectations of gender type behaviors.