The purpose of the research is to explore innovative trends in the development of Digital Society. The fundamental theoretical foundations of the study are applied for the analysis of social innovation in the evolution of Digital Society: The Сross Disciplinary Discourse, Fractal Theory and the Theory of Organizational Development of B. Livehud and F. Glazl. Organization and self-organization are considered as a synthesis of the two opposite processes. Self-organization as a stochastic process for creating social order creates conditions for the birth of innovation. The trends of evolutionary development of the Digital Society form the “fractal channels” of diffusion new Parameters of the Order. Three innovative trends in the development of the Digital Society are substantiated: The demand for Creative Human in the digital society; the phenomenon of Virtual Collective Subjectivity in digital space; the elements of Subjectivity of artificially created actors using artificial intelligence (Techno-Subjects). Three innovative trends determine the contradictory development of the Digital Society. The high riskogenicity of the Digital Society is a consequence of these contradictions. To harmonize the development of the Digital Society, it is necessary to develop digital social institutions that will determine in the new social order the rules of conduct for all participants.