Often cited as a key school readiness indicator, Approaches to Learning (AtL) includes a wide variety of dispositions, behaviors, and characteristics such as curiosity, initiative, cooperation, attention, persistence, and frustration tolerance. Children with AtL may interact more positively with teachers or may be able to sustain attention and focus during interactions, which increases the likelihood that they will learn from these interactions. Nevertheless, the construct of AtL suffers from a lack of conceptual and measurement clarity related to its use as an umbrella construct. The aims of this study were to explore measurement issues related to AtL, examine how play supports the development of AtL, and to investigate profiles of AtL among a group of children. Considering this, a careful review of the literature related to AtL was presented, including the ways in which the construct has been termed, operationalized, and measured. Using a newly designed conceptual framework, studied were re-examined to understand measurement issues related to AtL. Next, classroom implications for the construct of AtL were explored using two kinds of play, exploration and dramatization. Vygotsky’s work regarding young children’s working theories and symbolic representation was discussed as well as ways in which teachers can use curriculum to amplify children’s initiative, curiosity, and flexibility. While play-based curricula support children’s AtL development, more work is needed to understand how individual children develop AtL in the classroom. To that end, Latent Profile Analysis was presented examining profiles of AtL using a sample of Head Start Children. Results from the study revealed five unique profiles, including positive, negative, and low AtL, lending support to the idea that children develop AtL through multiple pathways.