High street fashion is an important industry in economic as well as aesthetic and cultural terms. Fashions not only provide a social language based on easily recognized, high-circulating items but they also generate massive wealth. These visual icons and images globalize human experience to a significant extent while, at the same time, remaining problematic to read. For example, how well-recognized and globally accepted are the meanings around images of a full red-lipsticked mouth, an unbuttoned pristine business shirt, or spiked multi-coloured hair The history of the visual suggests that every image has multiple readings; there is no essence to the image, no limits to its commentary, no reassuring boundaries restricting its suggestions. The image is ubiquitous, problematic and enduringly pleasurable, even as its meanings are tantalizingly concealed. A fascinating example is explored in this article of the ethno-methodological folly of the late 1960s, when a hormone pill-popping young man convinced a myopic medical team to undertake the desired surgical reassignment of his gender. The con was affected on the basis of a skilful and smooth gender-bending performance that rested on the persuasiveness of the unreliable image.