Assuming the importance of a “socioeconomic mosaic” influencing soil and land degradation at the landscape scale, spatial contexts should be considered in the analysis of desertification risk as a base for the design of appropriate counteracting strategies. A holistic approach grounded on a multi-scale qualitative and quantitative assessment is required to identify optimal development strategies regulating the socioeconomic dimensions of land degradation. In the last few decades, the operational thinking at the base of a comprehensive, holistic theory of land degradation evolved toward many different conceptual steps. Moving from empirical, qualitative and unstructured frameworks to a more structured, rational and articulated thinking, such theoretical approaches have been usually oriented toward complex and non-linear dynamics benefiting from progressive and refined approximations. Based on these premises, eleven disciplinary approaches were identified and commented extensively on in the present study, and were classified along a gradient of increasing complexity, from more qualitative and de-structured frameworks to more articulated, non-linear thinking aimed at interpreting the intrinsic fragmentation and heterogeneity of environmental and socioeconomic processes underlying land degradation. Identifying, reviewing and classifying such approaches demonstrated that the evolution of global thinking in land degradation was intimately non-linear, developing narrative and deductive approaches together with inferential, experimentally oriented visions. Focusing specifically on advanced economies in the world, our review contributes to systematize multiple—sometimes entropic—interpretations of desertification processes into a more organized framework, giving value to methodological interplays and specific interpretations of the latent processes underlying land degradation.