Humanity living far beyond its planetary boundaries has galvanised a desperate scramble toward sustainability, in all its socio-economic-ecological complexity. In increasingly fragmented global(ised) arenas, however, the sustainable growth trajectories of second-hand clothing production/consumption systems have proven non-linear, disjunctive and paradox-laden. The present thesis carves out epistemic space for exploring how these exacting paradoxes are both productive of and produced by circular fashion economies. Through a place-attuned, multi-scalar and relational lens, my investigatory scope is framed by two understudied geographies of second-hand apparel trade - the mitumba industry in East Africa, and e-marketplace platforms in the Global North context. Interweaving the analytic threads of political ecology, decolonial theory and feminist reflexivity, I undertake a cross-case comparative analysis to consider: between the global, national and local, how does the notion of second-handedness refract the lifeworld of differently-located and differently-embodied actors? Navigating the complex discursive terrain of greenwashing, I first de/reconstruct self-congratulatory corporate rhetoric which deliberately conflates ‘circularity’ with ‘sustainability’. By repoliticising human/environment encounters against the grain of technocratic dogma, the viscerally embodied realities of mainstream development interventions are explicated and enlivened - rather than elided and erased. In the spirit of reflexivity, my questioning framework also attends to (im)possible moments of alterity, agency and alliance-building instantiated in/through second-hand clothing marketplaces. In juxtaposing hegemonically-framed developmentalist discourses with personal counter-narratives emerging from the ground, the resulting picture is nuanced, messy and contextually-situated. The succeeding conclusion I draw is thus demonstrative and generative of such nuance. Sustainable fashion development need not be considered an end-in-itself, but instead an enduring means to an end - however imperfect and challenging. Scholars, practitioners and activists must collectively resist apocalyptic imaginaries, which prematurely foreclose political horizons for (co-)constructing alternative Anthropocene futures