The article examines the evolution of views of domestic planners and researchers of urban development on the so-called «historical city» during the 20th century. The design of the opposition «old»/ «new city» at the beginning of the 20th century is traced. Special attention is paid to the first conceptual work on the mentioned topic by the Kyiv municipal official A. N. Aristov, «Kyiv as an architectural and artistic city» (1918). Expanding his, so to speak, landscape considerations, Aristov singled out factors that must be taken into account in urban planning. Comparing the views of centuries ago with the current state of affairs, our investigation outlines the methodological prerequisites for the study of the urban development of the historical city, as well as a significant change in the views of domestic researchers and designers regarding the urban heritage of the second half of the 19th - early 20th centuries, which is the most actively took place in the 1970s and 1980s. An important summary of the research of the last quarter of the 20th century. was the formation of historical and architectural protection zones of Kyiv, the allocation of the confluence of the Dnieper and Lybіd rivers as a natural border of the conscious development of the city at the end of the 19th and the beginning of the 20th centuries, where the most valuable and integral urban development that took place before the beginning of the 20th century is located. and covers the plateau between the Dnieper and the Lybіd valley. The urban planning analysis of this planning structure, which stretched across the plateau along the Dnieper from north to south, determines the main distinguishing feature of Kyiv is its expedient urban planning linear system. Highlighting the natural-organic and four-dimensional spatio-temporal character of this system, this position is illustrated by a peculiar parade of hills: high-altitude dominants are located at certain spatio-temporal intervals from each other (half an hour or an hour's walk) in such a way that they do not "overlap" one another with visual perception, without suppressing or obscuring anything, and flowing like different themes in a melody, they create a single architectural and artistic composition. At the same time, already in ancient times, Kyiv was a constellation of settlements – a prototype of future satellite cities. Let's emphasize that the development of urban planning opportunities embedded in this system remains an urgent modern task. The author's personal contribution is the classification of artistic, methodological and organizational proposals of A. N. Aristov's concept. Town planning centers that should be taken into account in urban planning: architectural and artistic, scenic and poetic points. The article characterizes and defines the principle urban planning locations in the process of building the architectural and artistic structure of Kyiv; clarified the organizational provisions of Aristov's architectural and artistic concept with the proposal of new management structures up to the creation of modern structures such as the City Architectural and Planning Office.