There is a demonstrated discrepancy between consumers’ environmental consciousness and actual purchasing behaviors in relation to clothing consumption. To better understand this phenomenon and identify the challenges that millennials face in their experience with sustainable fashion brands, a study involving qualitative interviews was conducted to gather in-depth data on the firsthand experiences of the participants, fifteen current or recently graduated University of Chicago students at the time of the interviews. Through data analysis and abductive reasoning, six key themes were identified across the interviews, which altogether provided a more holistic overview of millennials’ clothing consumption. Lastly, the qualitative data informed the researcher in generating insight regarding potential ways in which sustainable fashion could more successfully target millennials, including improved marketing strategies, education, and universal certification labels.