Bootstrap Your Uncertainty: Adaptive Robust Classification Driven by Optimal-Transport

Distributionally Robust Optimization (DRO) offers a promising framework by optimizing worst-case performance over a set of candidate distributions, referred to as the uncertainty set. However, the efficacy of DRO heavily depends on the design of the uncertainty set, and existing methods often perform suboptimally due to an inappropriate or inflexible uncertainty set. In this work, we first propose a novel perspective that casts entropy-regularized Wasserstein DRO as a dynamic process of distributional exploration and semantic alignment, both driven by optimal transport (OT). This unified viewpoint yields two key new techniques: semantic calibration, which bootstraps semantically meaningful transport costs via inverse OT, and adaptive refinement, which adjusts uncertainty set using OT-driven feedback. Together, these components form an exploration-and-feedback system, where the transport costs and uncertainty set evolve jointly during training, enabling the model to better adapt to potential distribution shifts. Moreover, we provide an in-depth analysis of this adaptive process and prove theoretical guarantees of convergence. Finally, we present our experimental results across diverse distribution shift scenarios, which demonstrate that our approach significantly outperforms existing methods, achieving state-ofthe-art robustness.