My Princess Boy by Cheryl Kilodavis
Plot Summary: A heartwarming book about unconditional love and one remarkable family. Dyson loves pink, sparkly things. Sometimes he wears dresses. Sometimes he wears jeans. He likes to wear his princess tiara, even when climbing trees. He’s a Princess Boy. Inspired by the author’s son, and by her own initial struggles to understand, this heartwarming book is a call for tolerance and an end to bullying and judgments. The world is a brighter place when we accept everyone for who they are.
Youtube link: https://www.youtube.com/watch?v=9VhgLGq7bmo
Told from the mother’s point of view, the book sets up a male character who crosses gender lines. My princess boy wears dresses AND climbs trees with boys and girls. The author, perhaps in response to people who didn’t support her son, asks in an accusatory way near the end of the book, “If you see a princess boy, will you laugh at him, will you call him a name, will you play with him, will you like him for who he is?” That part could come across as preachy, but the book as a whole does a good job at setting up a middle ground for kids to express gender freely.