This paper offers a close reading of two works, Eleanor Estes' "The Hundred Dresses" (1944) and Marcus Ewert's "10,000 Dresses" (2008), that feature in current anti-bullying campaigns. Starting with "The Hundred Dresses," this essay examines how Estes' use of the school story not only exposes the social dynamics of relational aggression but also suggests how girls develop a sense of identity that is profoundly intersubjective. Focused on the development of the artist as a young girl, "The Hundred Dresses" not surprisingly reveals the importance of language and speech acts in the construction of self as well as social relationships. The paper then argues that "10,000 Dresses," written more than 60 years later, returns to the preoccupation with creativity, subjectivity, and conformity in "The Hundred Dresses" so as to redefine conventional ideas of gender and to make room for transgendered subjectivity. In approaching these two literary works, this essay draws on work concerned with psychological and social constructions of gender and identity in children.