This study investigated the rate of literate language feature (LLF) use in preschool age children with specific language impairment (SLI; n = 15), and typically developing language (TDL; n = 15). Language samples from two groups of children were compared in play and storybook sharing contexts with their mothers to determine whether there were differences in their LLF use. A multivariate within- and between-subjects design was used to assess preschoolers on five LLF dimensions of simple elaborated noun phrases (SENP), complex elaborated noun phrases (CENP), adverbs (ADV), conjunctions (CONJ), and mental and linguistic verbs (MLV), and on the summed LLF composite in play and storybook sharing contexts. In the LLF composite there was an interaction effect. Children with TDL had a higher rate of LLF use in play than in the story context, and children with SLI were significantly lower in their LLF use across contexts. When LLF dimensions were analyzed there was a main effect for context for the dimensions of CENP and ADV. Children had a significantly higher rate of these features in play than in the story context. In addition, there was an interaction effect for context by group for CONJ. Significance testing revealed that children with TDL used a higher rate of CONJ in play than children with SLI; however, in story, there were no significant differences between groups. The findings have implications in areas of language and literacy and assessment and measurement with children.