This thesis examines how the technical fit of a garment can affect an individual’s ability to fit in. It challenges the tool box used by practitioners working with anthropometric data (the surface measurements of the human body) and has produced new methods that are less reliant on published averages. Some of the thesis questions are: how does anthropometric data and the study of human anatomy influence notions of an ideal body? In what ways do anthropometric data and patternmaking principles include or exclude diverse body types? What tools can be developed to assist designing for diverse bodies? It takes a multi-method and multi-theory approach to the research and investigates concepts of fit through phenomenology, semiotics and anatomy. By exploring experimental methods in cut, it challenges the meaning of a key example of conservatism and uniformity in tailoring, the grey flannel suit.