In his book, The Fashion System, Barthes offers a thorough analysis of the sign system of fashion to show how the rhetoric of the signifier – the vestimentary structure signifying itself –, the rhetoric of the signified – representation of clothes to the outside world –, and the rhetoric of the sign – the rationale behind the existence of fashion –, all work to make the codes of fashion into a law. This proclamation of law in fashion, or the tyranny of fashion in Barthes terms, is also a way of distancing it, where fashion acknowledges and masks the arbitrariness of its decisions. Taking a cue from Barthes’ The Fashion System, my paper demonstrates the signifying system of Coco Chanel’s fashion as seen in Chanel’s advertising images –  in Man Ray’s photographs, and her clothing in fashion magazines.   Barthes tells us that fashion becomes successful by removing the sense of value attached to clothes the moment that value becomes shared. Chanel was the champion of this technique, and Barthes model allows us to see the method in her magic. It is the constraint in fashion, Barthes claims, that gives it meaning and freedom. The play of juxtaposition in surrealist aesthetic is found in Coco Chanel’s clothing. My paper draws from Barthes’ “variants of existence” and “variants of relation”, to investigate parallels between Chanel’s clothing and Surrealism’s philosophy of art in the age of mass culture. My paper examines relation between Chanel’s style of negotiating Surrealist art in her clothing – the androgynous figure of the dandy, primacy of the emotion over the intellect, the role of primitivism, the elements of the bizarre, the public persona of the artists (Dali, Duchamp, and Man Ray) – through Barthes model.