In the 21st century the Japanese postmodern concept of kawaii aesthetics has been the focus of the research of cultural anthropologists, sociologists, linguists and philosophers. Kawaii or “cute” is a phenomenon that could be manifested in different forms – as toys and mascots, or design and fashion, but also behaviour and relationship could be described as kawaii. While several authors have explained the aesthetics of kawaii as being a part of pop culture and avant-garde tradition, or a product of Japanese post-industrial society, this paper aims to offer a definition of the aesthetic category of kawaii from two different angles, opposing both the early modern Japanese aesthetic concept iki and a Western cultural invention kitsch that originated in German culture during the same era (19thcentury). In this paper, firstly, the concept of kawaii will be juxtaposed with the Edo period iki aesthetics that was structurally analyzed in the well-known work Iki no kōzō (The Structure of Iki, 1930) by Kuki Shūzō, a Japanese philosopher. The Iki aesthetics, which concern certain body postures, movement patterns, and behaviour, was the foundation for the emergence of the next Japanese aesthetic concept, the modern ero-guro (erotic and grotesque) mass culture, which focused on the commercial beautification of various objects (and persons as objects). In order to observe how the postmodern kawaii aesthetics developed through the transformation of kitsch-like ero-guro concept into the contemporary global aesthetics of mass production, this paper then compares and analyzes the manifold manifestations of kitsch and kawaii. The result will be an outline of a structure of kawaii that brings together different cultural, societal and aesthetic concepts.