In the Caribbean, the practice of getting dressed matters because it is a practice of attending to the body. Under a colonial regime, black bodies were ill-treated and selves were negated. Clothing played an instrumental role in the abuse of bodies and the stripping of a sense of well-being. Attire was one key way of demarcating master and slave and rendering some members of society null and void. Enslaved Africans, who were forcibly brought across the Atlantic to the New World, were considered chattel or commodities rather than people and clothes functioned in a way that reinforced that notion. Yet, dress became a strategy of subversion – of making chattel, property or ‘non-people’ look like people. The enslaved recognised that, through clothes, it was possible to look and feel free. Today that legacy remains. Clothing is seen not only as that which can make a people ‘look like people’ but also feel like people – clothing sets up a specific structure of feeling. This paper pivots on notions of looking and feeling like people while deploying Joanne Entwistle’s conceptual framework of dress as situated bodily practice. The article locates its investigation in the Caribbean, examining the philosophy and practice of Trinidadian clothing designer Robert Young. The article establishes him as a source of aesthetic therapeutic solutions in the Caribbean. It argues that his clothing designs produce a therapeutic discourse on the Black Caribbean body – a discourse, which facilitates a practice of getting dressed that gives a sense of agency, self-empowerment and psychic security even if that sense is embodied temporarily; lasting perhaps only as long as the garment is worn.