Do popular children’s books tend to reflect gender stereotypes, and do parents prefer their daughters to read books reflecting this pattern? We explored these research questions using the popular Roger Hargreaves’ Mr. Men and Little Miss collection of children’s storybooks, which is a series of individual stories all titled with and based on a binarized gendered character (e.g., Mr. Greedy, Little Miss Sunshine). Using a deductive content analysis approach, Study 1 revealed that the characters in the series’ 81 books tend to behave in gender stereotypical ways, with male characters more adventurous and active and female characters more domestic and passive. Books that had female leads were also more likely to have male secondary characters. In Study 2, participants rated the masculinity/femininity and positivity/negativity of the traits of each of the book series’ titular main characters without knowing the (gendered) book title. The traits used in Little Miss stories were associated with femininity, and the Mr Men story traits with masculinity. In Study 3, when faced with the prospect of selecting a Little Miss book to read to their daughter, parents preferred counter-stereotypical book choices (e.g., Little Miss Brainy). Perceived consistency with what parents wanted to teach their daughters about women predicted this book choice. Overall, although these books tended to reflect traditional gender stereotypes (Studies 1, 2), and people held these beliefs (Study 3), we found that parents wanted a counter-stereotypical book for their daughter. Implications for the transmission of gender stereotypes via children’s literature and parental choices are discussed.