This is a study of the related concepts of radical fashion and radical fashion innovation. Radical fashions are defined here as those that may never enter the market at all, and exist primarily on runway shows, in exhibitions and in publicity; by contrast, radical fashion innovations may be very successful in the marketplace. Radical fashions represent a clear break from the old designs, as opposed to incremental fashions, which are defined as an extension or evolution of the old designs. Using this definition, radical fashion seems to be at odds with the definition of marketable fashion. Nevertheless, while most radical fashions do not enter the market at all and live only in runway shows, exhibitions, and museums, there are many examples of radical fashion innovations successful in the market. Accordingly, a series of questions rise: What is radical fashion? What is radical fashion innovation? What are the differences and similarities between these, and how are they connected? This study seeks to address these questions, using a foundation developed in the radical product innovation literature. Fashion innovations may be in terms form or function, or style, and can be radical (involving the breaking down of old ideas) or incremental (involving the evolution of new ideas from old ideas). We draw from the radical product innovation literature to build two related models. The first is a model of radical fashion and radical fashion innovation that illustrates the components of both concepts. The second is a model of radical fashion innovation diffusion, drawn from the general product innovation diffusion literature, which explores the evolution of and the connections between these two concepts from the beginning (i.e., the radical fashion) to the end (i.e., success in the mass market). Radical fashion may result in designs that are more suitable for the runway, catalogues, or even museum display, than for actual wear. Radical fashion has sometimes been called “new ideas before their marketing phase.” Radical fashion may successfully enter the market, however, and gain wide acceptance among consumers. The transition from radical fashion to radical fashion innovation is not too different from the transition from invention to innovation, which is familiar to researchers in product innovation. Notable in this transition process is the fact that, for many product innovations, what drives the first customers to purchase (the “Visionaries,” to use Moore’s terminology in his “crossing the chasm” model of innovation diffusion) may be very different from what drives the rest of the market (the “Pragmatists.”). If this “chasm” or divide between the two market segments is not recognized, the innovating firm may find that their product stalls during the diffusion process and never effectively reaches the mass market. In the case of fashion products, visionaries (such as celebrities and the fashion press) prime the market and create favorable word of mouth; yet, at the same time, less-radical, wearable designs may be seen on the runway, or may be manufactured for the mass market and sold through department stores, specialty clothing stores, or even discounters. The most successful worldwide designers instinctively know this, and can continuously produce radically innovative fashion which also usually transitions to the mass market successfully. They recognize the need to reach the visionaries successfully to generate sufficient publicity and word of mouth, and also to use product design, promotion, and distribution strategies, as well as appropriate price lining policies, to reach the mass market (the pragmatists) effectively. We conclude with generalized findings and managerial implications for firms in the fashion industry. We attempt to bring the radical innovation literature, and its understanding of the process of radical innovation diffusion in the marketplace, to the expanding discussion of fashion marketing success strategic development.