Discourse in philosophy on fashion is relatively thin, this, in alignment with the typical disdain for clothing and dress from this field of study. However, there is some research that measures clothing brand addiction, attachment, digital culture, self-concept, and fashion communication. I aim to add to this research, particularly to the critique of fast fashion, to inform further philosophical conversations on the practice of dress, and not only argue that self-expression and sustainability can be best realized through second-hand shopping but that consumers have a moral obligation to do so, given the surplus material supply in existence. I will continue literature reviews of journal articles by philosophers, sociologists, and psychologists, and will also apply for funding to attend the American Society for Aesthetics conference where I will attend presentations on aesthetics, ethics, artistic, social, and environmental value, as well as conduct interviews with members who attend. I will also conduct interviews with various professors and students at USD on their dress and values. My findings will be mixed testimonies including claims of dressing for functionality, self-expression, and varying ideas of the value to dressing sustainably. With this data, I argue that clothing is intimately linked to personal identity, so dressing the body involves action and deliberation; I argue that this deliberation must attend to moral considerations. These include, how necessary one needs a new garment(s), who made the particular piece(s), what is the motivation for buying, and the likelihood of finding this piece(s) at a second-hand store