Although there are many views on the nature of wisdom, a common thread emerging in philosophical, folk, and scientific discourse is the importance of wise reflection or “reasoning” for sound judgment. In this chapter, we briefly highlight this common thread in historical perspectives on wisdom before moving on to discuss its further development through contemporary personality- and performance-oriented traditions in the empirical study of wisdom. These empirical traditions serve as forerunners to the recent methodological and experimental innovations in the study of wise reasoning. We detail the strengths and weaknesses of existing measures of wisdom, and the subsequent development and validation of the Situated Wise Reasoning Scale to address the limitations of previous approaches. We highlight work demonstrating the importance of the situation for measuring wise reasoning. Further, we address cultural differences in wise reasoning, and highlight ways to boost people’s propensity to reason wisely. Finally, we outline some of the theoretical and practical implications of wise reasoning for wisdom writ large.