American landscape architect Ian L. McHarg developed an ecological planning theory and method for analyzing biophysical and sociocultural landscape characteristics and for evaluating these to determine suitable land uses. McHarg's classic 1969 text, Design with Nature brought ecological planning to a mass audience, and his suitability analysis method was widely adopted. The theory, however, was neglected, as McHarg himself noted in his preface to the twenty-fifth anniversary edition of the book. A half-century later, there remains a need for theories that address the fit between humans and their environments, especially given ongoing environmental concerns marked by complexity and uncertainty. A fresh look at McHarg's ambitious theory reveals it to have considerable depth, with much of its scientific foundation retaining relevance. It is unique in its capacity for connecting planning and design to ecology and evolutionary biology. In particular, energy, order, and disorder; adaptation; health; creativity; and human agency were addressed by McHarg, and these concepts remain integral to environmental problem-solving today. Using McHarg's writings as the basis for a detailed analysis, we explore the meaning and significance of McHarg's parallel constructs: syntropic fitness-health and entropic misfitting-morbidity and death. The theory is placed in the historical and contemporary contexts of environmental planning and the science of ecology. Criticisms of McHarg's theory are addressed, and outdated aspects are identified. We connect relevant parts of the theory to socio-ecological practice through clear explanation of abstract concepts and identification of themes important for resilience planning and adaptive design.Keywords Adaptation · Resilience · Adaptive design · Ecological planning · Theory and practice "So there is a new task-to understand the way the world works, regulate behavior in response to this knowledge, restore the earth, green the earth, heal the earth."-Ian L. McHarg (1992, p. vi) preface to the 1992 edition of Design with Nature
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