Children’s literature provides a critical method of socialization and familiarization with gender roles, providing examples, boundaries, and limitations for gender identity construction. While extensive research has been done on how children’s literature depicts both traditional and non-traditional gender roles, very little research has been published on the cultural differences between literary representations. The aim of the present paper is to describe the representations of social roles of men and women in American, Czech, and Spanish children’s books published between 2010 and 2020. Three best-selling children’s picture books from each year from each respective culture were selected and analyzed, culminating in a thematic analysis of ninety-nine books. Using inductive thematic analysis, the study found all three cultures to be conservative in their depictions of gender roles, with Czech books as the most likely to feature traditional gender roles. Spanish books are more, and American books are the most subversive in their depiction of gender roles, containing an increasing number of non-traditional elements over an examined time period.