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Walter Benjamin reminds us throughout his work that progress and history are not linear but are a series of cycles that can revive the past in the present. As trends, whether in art, architecture, or fashion, recycle through time, we encounter opportunities for emancipatory change if we take advantage of the convalescence of past dreams and current technological and social development. This paper, then, aims to describe ways in which the past is present in the mundane by looking at moments in which memory (or ‘haunting’) is drawn upon in past social movements or usages of fashion clothing and connecting them with Benjamin’s concepts of the ‘angel of history’ and ‘tiger’s leap’ to discuss how their analysis provides opportunities to theorize emancipatory uses of fashion in the future. The paper will be oriented towards what looking at usages and references to the past and memory can contribute to an egalitarian and emancipatory fashion. Topics, and events, that will be explored include women’s use of fashion accessories for rebellion in post-colonial Argentina, vintage revivalism in the 1960s to today, subculture aesthetics, Civil Rights era protests, shirtwaist worker strikes, and contemporary runway shows and culture. By placing these diverse events in conversation with one another, the goal of this paper is to explore how memory is a valuable mechanism in political theorizing and paired with less-explored topics like sartorial fashion, can provide creative new approaches to how we articulate and organize for a more egalitarian society.