Children's picture books have been used in a variety of situations to introduce young children to unfamiliar experiences, including the transition to kindergarten. This study examines the ways in which children's transition to formal schooling is portrayed in 52 American picture books about starting kindergarten. Grounded in the ecological and dynamic model of the kindergarten transition, this content analysis explores the role of the entering kindergartner's family and the elementary school in supporting children during the kindergarten transition. Results show a high frequency of books (73%) depicting families (predominantly women) as supporting their children to start kindergarten and a low frequency of books (10%) depicting schools as supporting children and families with this transition. Kindergarten readiness skills were both discussed and performed in the home more often than they were mentioned or practiced in the kindergarten classroom, with an emphasis placed on children's social-emotional development and approaches to learning skills. Findings indicate a need for more picture books about starting kindergarten that portray a wider array of kindergarten transition experiences reflective of best practices for supporting children with the transition, and a diverse range of family constellations including families from various racial, ethnic, and sociodemographic backgrounds.