Caldecott medal winners have been recognized as best picture books, and they become one of the most predominantly selected literary works for children. Impacts they have on children’s emotional, social, and linguistic development are well-recognized in various areas such as literacy, literature, and sociology. As educational philosophies embedded in Caldecott medal winners may contribute to their ‘didactic’, sociocultural, and linguistic impacts, this study explores what educational philosophies are embodied in 85 Caldecott medal winners from 1938 to 2022. It classifies them in terms of five major educational philosophies (progressivism, essentialism, perennialism, existentialism, and postmodernism including multiculturalism, feminism, ecology, and metafictive devices). Finally, it traces their prevailing trends from the chronological order in which they are introduced. The findings of this study are as follows: 1) Some educational philosophies such as essentialism and multiculturalism have appeared most frequently while perennialism and progressivism are no longer prevalent modes presented in Caldecott winners; 2) The changes in overall chronological flows of educational philosophies are made from essentialism to postmodernism, especially promoting picture books of metafictive devices. This study assumes that using appropriate Caldecott winners that can meet children’s different educational needs would better result in their emotional, sociocultural, and linguistic development.