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​The purpose of this paper is to examine male characters’ cross-dressing experience in selected British and American children’s books. Cross-dressing motif in children’s literature has been used for female-to-male cross-dressing to resist against the male dominated social order and unfair treatment on women. Recently, children’s books that deal with male-to-female cross-dressing become more available. The books seem to reveal the male characters’ cross-dressing as an enjoyable incident in the uniform rather than serious gender related issue. The paper suggests that male cross-dressing narratives encourage to respect each individual’s choice of freedom and accept difference. Bakhtin describes carnival that seeks to liberate participants from temporary convention and established order with subversive function. The male cross-dressing motif produces humor, exaggeration, grotesque body, and parody to the established power and authority, which are important elements in carnival. The male cross-dressers, whether they enjoy their female experience or not, are able to look at the way in which boys and girls are treated differently. Adults need to think about their behavior in the construction of gender equality along with social relationships, which are strongly influential to children’s attitudes to gender.