This article is part of the 50th anniversary issue of the Journal of Vocational Behavior (JVB), with a focus on person-environment (P-E) fit. P-E fit has been a central research area in vocational and organizational psychology. With a focus on highly influential work in both fields, this article aims to synthesize P-E fit literature and develop theoretical models to guide future research. First, we summarize key perspectives and the state of the art in the general P-E fit literature. Second, based on a succinct review of P-E fit papers published in JVB, we take an interdisciplinary approach to critically discuss the conceptual and methodical ambiguities in this area. Third, we integrate identity and social exchange theories to present an Identity-Capability-Reward (ICR) model to conceptualize P-E fit across job roles and work entities at different levels. Fourth, we draw upon self-regulation and life-span development perspectives to propose a cybernetic development model that theorizes the self-regulated changes of fit experiences across time. We conclude with recommendations for an integrative, dynamic, and developmental approach to advance the P-E fit theories.