Lacanian critical theory provides invaluable resources for social critique, but must always do so by negotiating between its account of “constitutive” and “constituted” alienation – between the unavoidable forms of alienation involved in entering into socio-linguistic life, and the historical forms of alienation which arise due to particular social conditions. Theorising this connection remains necessary for a historically informed social critique which is nevertheless able to recognise the unavoidable structural forms of alienation of any such human society. Here, Robert Pippin’s Hegelian theorisation of alienation as a failure of self-reflexive social agency provides an important normative framework. Critique thus relies upon a particular image of “human nature”. The “natural” in “human nature”, however, cannot be separated from its emergence from “nature as such, against Pippin’s insistence on the strict separation between nature and spirit. Here, the role of “habit” in G.W.F. Hegel’s account of the transition from “nature” to “spirit” (or “second nature”) thus allows for critique to be grounded in the conditions of life itself. Drawing on findings from philosophical anthropology, and building upon what theorists such as Slavoj Žižek and Catherine Malabou identify as its transformative core, far from being mere unconscious repetition, habit rather represents a heuristic for critical social analysis attendant to the historical and transhistorical forms of social life, one cognisant to the relationship between constitutive and constituted alienation.