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The purpose of this article was to examine why men keep clothing that does not fit. Previous research with women suggests that clothes that do not fit are not simply thrown away, but may be kept as a reflection of the self. A web-based survey that prompted discussion of keeping ill-fitting clothing was completed by 76 men at a Midwestern university of all ages. The themes found were these clothes were kept for Weight Management, Investment Value, Sentimental Value and Functional Value. Young men made less reference to Weight Management than older ones. Younger men kept clothing for Sentimental Value with pleasant associations to childhood. Societal pressures to limit interaction with clothing were evident with responses such as finding function in ill-fitting clothing rather than purchasing new ones. However, identity was reflected in these choices. Further research with men is needed to fully understand clothing disposal practices among men.