Dewey’s notion of second nature is strictly connected with that of habit. I reconstruct the Hegelian heritage of this model and argue that habit qua second nature is understood by Dewey as a something which encompasses both the subjective and the objective dimension – individual dispositions and features of the objective natural and social environment. Secondly, the notion of habit qua second nature is used by Dewey both in a descriptive and in a critical sense and is as such a dialectical concept which connects “impulse” and “habit,” “original” or “native” and “acquired” nature, “first” and “second nature.” Thirdly, the ethical model of second nature as habituation and the aesthetic model of second nature as art are for Dewey not opposed to one another, since by distinguishing “routine” and “art” as two modes of habit, he makes space for an expressive and creative notion of second nature. Finally, I argue that the expressive dialectics of habit formation plays a crucial role in Dewey’s critical social philosophy and that first and second nature operate as benchmark concepts for his diagnosis of social pathologies.