The thesis inquires into the theme of political judgement and aims to rethink it from the perspective of twentieth-century philosophies of existence. It seeks to take up the contemporary challenge of political judgement that remains inadequately addressed within recent theorizing: how, given the modern breakdown of metaphysical absolutes, to reinvigorate the human capacity for political judgement as a practical activity able to confront the ambiguous, plural and complex character of our postfoundational world. Against this background, the thesis aspires to reclaim the distinctly historical orientation of twentieth-century existentialism, in particular the work of Jean-Paul Sartre, Simone de Beauvoir, Albert Camus and Hannah Arendt. It draws on their aesthetic sensibility to resuscitate the human judging ability in its worldly ambiguity and point towards an account of political judgement capable of facing up to the challenges of our plural and uncertain political reality. Retrieving their vigilant assumption of the situated, worldly condition of human political existence and the attendant perplexity of judging politically, the aim of the thesis is to suggest how the existentialists' insights can be brought to bear on contemporary problematics of political judgement that seem to elude the grasp of abstract standards and predetermined yardsticks.