The purpose of this study was to explore the relationships between businesswomen’s choice of professional dress and four dress perception variables (ie comfort, employment orientation, appearance labor, availability of professional dress). The choice of professional dress is viewed along the fashion continuum, which ranges from “classic dress” to “innovative dress.” A model was developed based on systems theory, and variables were selected from previous research that relate to an individual’s perception of and attitude toward their professional dress as well as an individual’s population characteristics. Data were collected via an online survey managed by a marketing research company. Results of the multiple regression analysis and mean comparisons testing indicated significant relationships between businesswomen’s choice of professional dress and comfort, appearance labor (ie effort devoted to attire), and availability of professional dress (ie limited store availability) as well as age and education. Based on the findings, academic and practical suggestions as well as recommendations for future research were provided.