It is noted that the thorough monograph of the famous English philosopher, historian of science, and art theorist R. G. Collingwood «The Principles of Art» consists of three «books», each of which covers a number of important issues of fundamental importance for history, art theory and cultural studies. From the point of view of time, it can be argued that R. G. Collingwood tried to link the content of the three «parts» of the monograph, emphasizing their overarching idea, i.e. the English scholar’s articulation of the integrity of the time dimensions «past — present». The phenomenon of «integrity» is the basis for harmonizing the theoretical material of all three «components» of the monograph «The Principles of Art». It is emphasized that the problematics of one of the chapters of the second «book», i.e. «The Theory of Imagination» is the basis for this article, which uses the potential of general scientific methods of analysis, such as historicism, systematization, comparison and generalization of the problem under study. The stated methods are based on the principle of a parity approach, which allows taking into account the experience of many humanities, including cultural studies, philosophy, psychology, and art history. It is emphasized that the analysis of both «illusory feelings» and a number of other related issues actualizes the problem of the conceptual and categorical apparatus, generally necessitating the argumentation of new concepts. «The Principles of Art» demonstrates, firstly, R. G. Collingwood’s constant interest in upgrading the means of researching humanitarian knowledge, secondly, his attempts not to destroy the connection between the Greco-Roman tradition of thinking and modern European humanism by preserving the basic conceptual and categorical structures, and thirdly, the constant use of samples of interpretation of «transcultural» concepts in European languages, which greatly complicates the research process of adapting Collingwood’s ideas. The article proposes the author’s model of interpretation of the stated problems but takes into account the experience of R. G. Collingwood in the double operation of certain concepts, which in particular concerns the concept of «illusion», which means both the «illusion of play» and the structural element of the theory of imagination. The historical and philosophical tradition of understanding segments of the heritage of R. Descartes and John Locke is recreated, and the historical and philosophical material is presented based on the principles of a personalized approach, which is defined as the cornerstone of the logic of cultural analysis.