This thesis analyzes the social significance of the abstract phenomenon of fashion, with reference to sartorial examples from the Fashion industry, using Walter Benjamin's writing on surrealism and fashion as a theoretical model. Examples primarily come from "deconstructive" designers including Martin Margiela and Rei Kawakubo, and post-deconstruction designers such as Jun Takahashi and everyday wearers who make or remake their own garments at home. Benjamin's arguments are presented in terms of his wider political project, demonstrating the continued relevance of his thought in understanding contemporary aesthetic, commercial and material practices. In addition, the thesis refers Georg Simmel and Ernst Bloch, as well as historian Pierre Nora, in order to define the relations between past and present, making and wearing, and production and consumption in "deconstructive" garments. The thesis accompanies an exhibition of clothing, texts and images entitled "Made with Love: Fashion, Craft, and Other Beautiful Illusions," which was held from May 21st to 27th, 2005 in an empty retail space in Ithaca, New York. Mounting the show and collecting feedback from it formed the concepts in the thesis, while the writing underpinned the ideas in the show. The simultaneous exploration both in writing and fashion gives the rhetorical argument immediate practical relevance, while providing the practice with a theoretical armature, already far more composed than is usual in fashion design. The interdisciplinary nature of this study links and expands the theoretical study of material culture and the practice of idea-led design.