Lacan and Winnicott are both profoundly psychosocial thinkers who shared an interest in the modern psyche and the alienation often considered endemic to it. From Freud, Lacan took the theory of narcissism (Borch-Jacobsen, 1991), which he developed into a wide-ranging critique of the psychosocial constitution of the modern subject. Winnicott, on the other hand, trained his eye on the environmental conditions necessary for feeling authentic, or 'real,' and the experiences that might produce alienation from this 'true' self, and encourage the formation of a narcissistic 'false' self (Donald W. Winnicott, 1990). In this context, Lacan and Winnicott's shared interest in the metaphor and function of the mirror, which has long provided an entry point for clinical and academic comparisons of their work, is a key point of orientation. This article seeks to explore and unpack the relationship between Lacan and Winnicott's interest in narcissism, alienation and the mirror, locating their thinking in relation to dominant philosophical conceptions of subjectivity and sociological understandings of modernity, dating from the seventeenth to the late nineteenth century. Situating Lacan and Winnicott on this terrain throws their theories of the mirror into relief in important ways. Not only is the 'modern' character of psychoanalysis foregrounded, the contribution it can make to social transformation is also affirmed.