Informal workers’ recent organizing efforts deserve our attention. They have defied the odds and launched alternative models that are more relevant to contemporary structures of globalized and neoliberal production than earlier industrial union-based organizing efforts. While some have succeeded in increasing protections and others have failed, all have relied on informal workers’ willingness to experiment with new organizational forms, rules, and definitions of work, identities, regulations, sectors, and populations. It is these experiments, we argue, that are crucial to ensuring a more just future for global labor. Drawing from fieldwork data collected among informal workers’ organizations in the garment manufacturing sectors of Brazil, India, and China, this article builds two hypotheses to explain the conditions that shape, facilitate, and/or hinder experimentation among informal workers of the global South. First, we propose that political conditions from above—namely, decentralized political administration/federalism, competition among political parties, and support from ruling governments and/or industrial unions—helped foster the necessary space for informal labor to undertake organizational experiments during the turn of the millennium. These conditions, in turn, interacted with nation-specific legacies of labor organization from below to shape particular forms. Second, we propose that changes in the political conditions from above can erode the space for labor’s organizing experimentation, but that the legacy of labor’s organizational experiments from below can also resist and reshape those very changes in political conditions. These findings offer hope for the possibilities of labor revitalization even under neoliberalism, but also a warning about the likely roadblocks to that revitalization.