Why has hedging become a uniquely prevalent foreign policy strategy in Southeast Asia? This article addresses that puzzle by applying the framework of Historical Institutionalism to analyze the deep-rooted historical foundations of Southeast Asian hedging. Moving beyond structural and domestic-level explanations rooted in neorealism and neoclassical realism, the study argues that Southeast Asia's preference for hedging is a product of path-dependent foreign policy trajectories shaped by two critical junctures: the colonial era and the Cold War. These periods entrenched a regional commitment to sovereignty and security, and a normative aversion to rigid alignment, two drivers of hedging behavior that continue to shape the foreign policies of Southeast Asian states. Drawing on case studies of Indonesia, Vietnam, and Thailand, the article shows how policy feedback mechanisms normalized flexible engagement and non-exclusivity as default strategies, while also illustrating how contemporary structural and domestic factors interact with historical legacies to produce diverse hedging patterns within the region.