Accurate donor-recipient allograft size matching remains a critical determinant of outcomes in lung transplantation, yet current approaches rely predominantly on predicted total lung capacity (pTLC) and height-based metrics derived from population-based equations. These simplified surrogates fail to capture individual anatomical variability, disease-specific alterations in thoracic geometry, and the spatial relationship between donor lungs and recipient chest cavities. In this review, we examine the limitations of conventional size matching and synthesize emerging evidence supporting imaging-based approaches, including computed tomography (CT) volumetry, radiomics, and machine learning. CT-derived volumetric analysis enables individualized anatomical assessment and has been associated with clinically relevant prediction of primary graft dysfunction and mortality. Advanced computational methods may further support extraction of imaging-derived features and integration with clinical data, although these approaches remain investigational. Collectively, these developments signal a paradigm shift from crude population-based metrics toward imaging-driven and computational approaches in the modern era. With rigorous validation and careful clinical integration, imaging-based approaches may complement conventional size metrics and support more individualized donor-recipient assessment.