Children constantly encounter signs during cultural practices, although many theories do not fully acknowledge sociocultural aspects of semiotic development. The author examines research on cultural practices and contexts in which children learn to produce signs involving representational drawing and pretend play. This work is contrasted with more individualistic views of semiotic development that fail to adequately address sociocultural aspects of semiotic functioning to varying degrees. The author also presents a theoretical model for understanding the structure of any sign system and for comparing semiotic systems, using examples from the drawing and pretense literatures. It is proposed that the sign-making practices in which children participate are shaped by a complex hierarchy of conventions.