Optimal distinctiveness – being both 'similar to' and 'different from' peers – is an important imperative of organizational life and represents a common research question of organizational scholars across various disciplinary domains such as strategy, organization theory, entrepreneurship, and international business. This Element reviews the historical grounding and recent development of optimal distinctiveness scholarship, based on which an orienting framework is proposed to stress the highly contextualized and dynamic nature of optimal distinctiveness. The orienting framework provides several powerful and unique angles for understanding organizations' competitive positioning in various types of markets, for applying optimal distinctiveness research to different levels of analysis, and for nurturing a more cross-disciplinary and mutually generative conversation on optimal distinctiveness theory.