This thesis explores the work and critical thought of Oscar Wilde from the perspective of postmodernism, and presents the argument that Wilde’s thinking can be read as strikingly similar to various postmodern approaches. It positions Wilde as a ‘proto-postmodernist’: not as a forerunner of postmodernism, nor a full postmodernist, but rather someone who employs ideas and practices that would now commonly be regarded as postmodern, but who had those ideas and engaged in those practices before postmodernism arrived on the scene. The thesis is divided into three parts, each of which groups similar theoretical fields in a discussion of similarities (and, sometimes, differences) between Wilde and postmodernism. In part one, the discussion moves from a basic look at binaries, though deconstruction, to a discussion of truth and falsehood in postmodernism. In part two, there is a discussion on simulacra, hyperreality, and postmodern ideas on surface and depth. Finally, the third part discusses the disappearance of a naturally delineated field of expertise by discussing intertextuality, word and music studies, moving finally to ekphrasis and postmodern theories on the photograph.