The chapter suggests and illustrates a methodological approach for understanding movement learning in order to explore and clarify the relation between how people learn and the environment in which they learn. Drawing on the work of John Dewey, the later works of Ludwig Wittgenstein and socio-cultural approaches, a practical epistemology analysis (PEA) with focus on aesthetic judgments is suggested as a way of developing a valuable approach for understanding learning in different social and cultural contexts. The approach is illustrated by an exploration of movement learning in educational settings such as skating as a child, playing exergames in school, playing international elite football, or running marathon as an aging man. As can be seen from these illustrations, the significance of aesthetic experience for learning is visible in the narratives. The fact that aesthetic judgments are used normatively to decide what is to be included and excluded in movement learning, and also that aesthetic judgements are used to make relation between the individual and his/her life as a whole, facilitates an understanding of the relation between the learner and the life situation in which learning is situated.