Traditional fairytales serve to socially construct gendered categories and reify dominant understandings of masculinities and femininities. Using reading groups and participant observations in an elementary school classroom, this article explores how children actively engage with gendered messages within fairytales--specifically examining children's adherence to, and negotiation of, gender boundaries as demonstrated through their performances of gender within daily classroom discussions and activities. This article illustrates the diverse ways in which children engage with text and how they apply these messages to their own lives, work within its confines, and explore alternatives. Findings demonstrate the potential for educators to create an environment through which children are afforded the freedom to navigate gendered messages and discourses. Such initiatives may contribute to developing more inclusive learning environments and educational opportunities that challenge the perpetuation and reinforcement of long-­established gender stereotypes in the classroom.