The aim of this article is to explore the relationship between aesthetics and pedagogy by focusing on the aesthetic design of reading books. The idea that multiple senses and activities interact when children learn to read is not new in educational studies. Research shows that children’s aesthetic experiences can contribute to increased learning outcome. In this article, we discuss the application of such considerations by examining two reading books in the Swedish series Vill du läsa? (1935–1936) and Nu ska vi läsa (1948–1949), thus taking a historical perspective on the topic. The books were illustrated by two of Sweden’s most famous artists, Elsa Beskow and Ingrid Vang Nyman. We examine how the books appeal to the reader’s creativity and playfulness. Our theoretical starting point is Walter Benjamin’s reflections on the reading and writing child where the gaze is also important. Benjamin’s thoughts were important for Swedish reform pedagogy, which in turn influenced the work of Elsa Beskow and Ingrid Vang Nyman. With the reform pedagogy’s celebration of the creative child, the focus shifts from the book as a product to the actual learning process for which the aesthetic is a prerequisite.