This paper is focused on the fashion and clothing decisions made by millennials at Bowdoin College. It aims at explaining the deeper motivations and underlying reasons for dress and style and, essentially, why people wear what they wear. The research I conducted can be explained in two different parts. The first method of data acquisition was in the form of a survey on Bowdoin’s qualtrics software. These surveys asked general questions about clothing and stylistic preferences in addition to perceptions of pressures and strains at Bowdoin from clothing. The surveys were then followed up by in-person interviews that investigated the reasons behind the survey responses. The results were wide ranging and illuminated some interesting tensions present at Bowdoin. More transparently, the price of clothing relates to people’s presentation of wealth and status, however there are also correlations between what people will and won’t wear to keep their association with certain groups on campus.