The author analyzes the special type of imagery, that is kaleidoscopic image, and investigates its evolution in photography, video and multimedia from the first vortograph (photo, taken through the prism of the mirrored glasses in 1917 by Alvin Langdon Coburn) until nowdays. The author combines empirical methods with the theoretical analysis. For the first time in the humanitarian historiography a huge package of kaleidoscopic photos, video and multimedia images was collected and systematized. The collection includes works of several dozens artists, some of them interviewed by the author of the research. As a result the author proposes the classification based on the subject regimentation: the entire aggregation of the assembled materials is divided into three main groups - the human body, the nature objects, the architecture. The images in each group are analyzed with respect to their structural features, composition and semantics, creation technology. Two structural features were singled out as unifying for all three groups: ambivalent character of the kaleidoscopic image as a symmetrically organized chaos, as well as a trend to transform a realistic recognizable subject into an abstract pattern. Kaleidoskoping is considered to be of the form generated mechanisms not only in the visual arts, but also in practice-oriented areas: design and graphic design, textile industry and fashion, ceramics, glass industry, etc.