<p>In response to institutional and competitive pressures, organizations must balance legitimacy and differentiation to achieve their strategic objectives. While research on optimal distinctiveness has made significant progress, a critical gap remains in understanding how organizations can strategically position themselves for optimal distinctiveness—especially as it evolves across multiple dimensions and under varying contingencies. This paper presents a systematic review that integrates insights from multidimensional and contingency perspectives to develop a comprehensive framework for achieving optimal distinctiveness. By incorporating organizational and environmental contingencies, our study refines the theoretical landscape and clarifies the boundary conditions of optimal distinctiveness. Adopting a multidimensional approach, we move beyond a narrow cognitive focus to address the inherent tension between legitimacy and differentiation. We further propose the spillover-buffer effect of legitimacy and differentiation to explain contingent strategic behaviors, expanding the strategic toolkit available to organizations. Specifically, we introduce five key strategies: multidimensional strategy, multilevel strategy, spillover-buffer strategy, audience diversity-fit strategy, and market category-fit strategy. These strategies offer novel pathways for organizations to navigate the complex interplay between legitimacy and differentiation, thereby enhancing their ability to achieve optimal distinctiveness.</p>