Aesthetic expression of dress was examined by interviewing 15 midwestern university students. The objective was to understand the style development process and the motivations for clothing selection. The responses of participants selecting clothing from a variety of purchasing locations were analyzed. The purchasing sources examined were vintage or used clothing stores, a variety of sources used by cross-shoppers, and mainstream or mass market locations. In-depth interviews were analyzed for content. Aesthetic themes or categories emerged that helped to define differences: event dressing, imaging gender, variety clothes versus signature clothes, apparel meanings, process of ensemble, and customization of clothing purchases. These categories were analyzed and compared with those identified in the literature and with postmodern characteristics outlined by Evans and Thornton (1989). Understanding individual motivations in aesthetic expression and sourcing locations will aid in the study of fashion change.