In everyday interaction interlocutors use pragmatic co-speech gestures to cooperatively construct conversation. Shrugs, one of the most common pragmatic gestures, communicate a remarkable array of seemingly unrelated or even contradictory meanings – agreement and disagreement, ignorance and obviousness, interest and disinterest, among others. Although shrugs are often among the earliest gestures acquired by American English-learning infants, children do not immediately use shrugs with the same variability of form and function as adults. Because shrugs are used both emblematically and interactively, they provide unique insight into pragmatic development. How do shrugs simultaneously function as conventionalized symbols and contextualized indices? How do children develop this pragmatic flexibility? Although there is a wealth of literature concerning gesture’s role in communicative development, existing research has primarily focused on topic gestures and left pragmatic gestures relatively understudied. Within the limited existing literature, pragmatic gestures are rarely given the same nuanced consideration afforded to topic gestures. There is an implicit assumption that meaningful differences in the role gestures play in early communication are present across categories of gesture but not within the class of pragmatic gesture.In this dissertation I use a corpus of spontaneous parent-child interaction and an annotation scheme grounded in principles of conversation analysis to explore how pragmatic gestures like shrugs operate in early communication. In three studies, I describe changes in form and function across early childhood and into adolescence. First, I show that the developmental trajectory of palm-up gestures in early childhood is functionally distinct from that of beat gestures. Second, I describe young children’s use of shrug gestures with and without speech. From these analyses, I propose that children initially produce shrugs as ignorance emblems and develop shrugs’ characteristic many-to-many form-function mapping in later language development. The third and final study explores this transition from emblematic to pragmatic use in early adolescence. Together, these studies demonstrate the necessity of accounting for gesture variation within the broad functional category of "pragmatic gestures" in communicative development. By looking both within and beyond early childhood, this dissertation contributes to our understanding of pragmatic development as fundamentally multimodal.