This essay aims at clarifying our understanding of human participation in sustainability transitions from the pragmatist aesthetics perspective. By sustainability transitions, I refer to processual changes that move towards enhanced environmental and/or social sustainability. At the risk of inappropriateness, I argue that the cultivation of aesthetic sensibility manifests in experiencing sustainability. To understand those ordinary experiences that convey vistas for sustainability transition management, I return to John Dewey’s Art as Experience (1934). I first show that Dewey’s conception of sensibility is two-sided, marking both adaptation and expression. Second, by building on the two sides of sensibility together with the contemporary pragmatist aesthetics discussion, I propose that aesthetic sensibility means a shared practice of attuning to transformation. My analysis suggests that acknowledging aesthetic sensibility in experiencing sustainability stands for a transition towards an enhanced conception of the human being as one whose ameliorative practices evolve in collaboration with other beings, living and non-living. For the fruition of sustainability transitions and subsequent expected transformations, aesthetic sensibility should then be acknowledged as a significant dimension of the sensory approach.