This article identifies and analyzes an emerging archive of children’s picture books that represent transgender and gender creative child characters. The subgenre of children’s literature is referred to as new queer children’s literature. The author explores the ways these texts represent queer youth as they negotiate various social institutions, especially the family and the school. It is suggested that an ambivalent reading of these images—one neither committed to anti-normativity nor assimilation—can help us understand the queer present at its most affirmative and, by extension, aid us in beginning to theorize possible queer futures.