This chapter describes the concept of learning flexibility in Experiential Learning Theory and its relationship to integrative learning and adult development. The Learning Flexibility Index (LFI), an improvement over previous measures of learning flexibility, is introduced. We introduce a new measure for calculating learning flexibility based on the Kendall’s Coefficient of Concordance or W. Construct validity for the LFI measure is shown by confirming six hypotheses about the place of the LFI in a nomological net. The LFI is negatively related to age and educational level. Women and those in concrete professions tend to be more flexible. Individuals with an assimilating learning style tend to be less flexible. Learning flexibility is positively related to Akrivou’s Integrative Development Scale. Discriminant validation of the LFI shows that adaptation of learning style to context in the LFI is different than random variation in the Kolb’s Learning Style Inventory (KLSI). Finally, a case studies of individuals with high and low LFI score illustrates how learning style and learning flexibility can combine to produce unique patterns of adaptation to different learning contexts. Implications for future research and practice are discussed.