My studio-based research plays with the concepts of disguise, the trickster archetype, sweet kitsch, and sentimentality to explore and reclaim male femininity. These topics are explored through a performance piece which contrasts the visual aesthetics of a Pierrot character I designed within a supermodern, non-place setting. This paper argues that the ethos behind sweet kitsch and sentimentality becomes significant when contrasted with the concept of non-places, chromophobia, and network sociality, all hallmarks of supermodernity. If supermodernity is concerned with efficiency and uniformity, and rejects expression and personal connectivity, then sweet kitsch is the remedy to the isolation and disconnect it creates. The purpose of this paper is to explore what it means to create a sense of belonging and to give oneself permission to exist in a space which is indifferent to interpersonal connection, and how the act of performing a Pierrot character within an environment which is hostile to interpersonal connection can generate meaningful connection within one’s life through sentimentality.