In contemporary advertising market, one of main trends is to speak surrealistic visual language which provides 'enjoyable spectacles'. Specially, in the beginning of 21st century, there discovered more and more exhibitions and discourses about surrealism reinterpreted from the viewpoint of postmodernism. Surrealism as a creative style of expression based upon free association, has been a great inspiration for fashion ads for commercial communication as well as fashion design since its origin. However, there has been ignored the idea of analyzing surrealistic image expressed in fashion ads in spite of their flood. Accordingly, the purpose of this study is to grasp its cultural meaning through analyzing aesthetic characteristics of surrealistic image expressed in fashion ads. It will provide a better understanding of surrealistic image in fashion ads reflecting popular taste and preference directly as popular visual culture, focusing on post modern context. A case study of surrealistic fashion ads limits to TV or print commercials and digital ads as image ads stimulating visual expressions. The Results can be summarized as follows. Surrealism is an avant garde style which deconstructs the established meaning system as well as the existing formalistic order and then put them together in the frame of 'dream' and 'unconsciousness'. Defamiliarization questioning the whole edifice of representation can be adapted to. By means of paradox and metaphor, unfamiliar new visual world can be represented. The plastic characteristics of surrealistic image in fashion ads are founded as surrealistic styling of time and space, distortion of object by methods of automatism, depaysement, parody and trompe-l'oeil which bring about the deconstruction of gestalt. Aesthetic values of surrealistic fashion ads appear as dualistic representation, allegoric symbolism, fantastic romanticism. Ultimately they lead to marvelous. mysterious, humorous visual effects. Foster reinterpreted these effects of surrealism from Freud's 'Uncanny Concept'. 'Uncanny' means the phenomenon recurring to familiar being defamiliarized by repression. Surrealistic fashion ads strengthen this shocking effect more and more dramatically in company with our post modern needs for fantastic adventure and thrilling spectacle. It can be thought that surrealistic fashion ads reflects uncanny as an alternative which can relieve us of our stress and anxiety and which realize our potential desire in contemporary post industrial stage.