Lewis Carroll's Alice's Adventures in Wonderland (1865) and Through the Looking-Glass (1871) and Carlo Collodi's Le Avventure di Pinocchio (1883) are among the most influential classics of children's literature. Firmly rooted in their respective British and Italian national cultures, the Alice and Pinocchio stories connected to a worldwide audience almost like folktales and fairy tales and have become fixtures of postmodernism. Although they come from radically different political and social backgrounds, the texts share surprising similarities. This comparative reading explores their imagery and history, and discusses them in the broader context of British and Italian children's stories.