Play has a significant role in language and literacy learning. However, even when valued in schools, opportunities for play are limited beyond early childhood education. This study of an after-school program for adolescents looks closely at several forms of play that students engaged in to produce self-portraits. The study suggests that play and experimentation with visual texts, tools, spaces, peers, and materials contributed to students' engagement with complex visual literacy practices. Two important implications are discussed: (1) that learning through play is a participatory, inclusive approach to literacy that invites adolescent students, even those often reticent to take risks, to cultivate literacy practices and identities; and (2) that visual modes of literacy play and production enable an experiential understanding of academic literacy concepts adaptable to other modalities and contexts.