This qualitative case study investigated how two White female preschool teachers, who were familiar with anti-bias pedagogy, discussed gender non-conformity using a book in their classrooms. The book discussions were audio-recorded and transcribed. Teachers challenged some of the children’s gender stereotypes about gender non-conformity; however, teachers did not counter other stereotypes and kept discussions about gender non-conformity at the surface level. Children drew on their normative understandings of gender as a binary concept to make sense of gender non-conformity. Children were aware of gender-stereotyped clothing that would be deemed gender appropriate by their peers or family. Some children had difficulty understanding why a boy would wear a dress, while others challenged gender stereotypes. Teachers did not engage in in-depth discussions around gender non-conformity or around the gendered nature of bullying of a ‘girly’ boy in the book. Implications are discussed for teacher professional development and for gender-affirming early childhood pedagogy. (author abstract)