This chapter revisits Bourdieu’s concept of habitus in relation to the American pragmatist philosopher John Dewey’s understanding of the role of habit in making sense of social life. Both had a keen appreciation of the links between the social, the practical, the contextual and the historical. However, whereas Dewey viewed the ideal society as one constructed through cooperative public interaction and the increasingly shared habits of individuals, Bourdieu’s theory involves a more systematic and empirically rich critique of power and the basic structures that constitute society, de-emphasizing discursive acts as a means for restructuring the habitus. Alluding to the influences of phenomenological and pragmatist philosophy on their respective views, the paper explores important similarities and differences in their understanding of the role of habit and habitus to create, sustain or challenge social order. Finally, through a case study, it considers the importance of theory distinct perspectives for a more rigorous conceptualization in translation and interpreting studies of meaning negotiation, especially in the face of opposing communicative objectives and imbalances of political or discursive power.