Consumers have greater purchase choice options to fulfill their wants and desires in a networked world. In the United States fashion business, privately owned brick-and-mortar fashion boutiques face the unique challenge of strategically competing with online retailers who usually have low overheads and inventories. Low adaptability,limited innovation, and inadequate attention to a changing marketing landscape could be responsible for the decline in the survival rate of several traditional, or pure brick-and-mortar fashion boutiques. Newer approaches may be essential for traditional and online entrepreneurs, to increase adaptability and business sustainability and in increasing customer marketing outreach. Grounded in the general systems theory, the research conducted in this qualitative study was with the invocation of a multiple case design and entailed gaining insight into the exploration of strategies used by successful brick-and-mortar fashion boutique owners in contending with the purely online retailers. Semi-structured interviews constituted the means for data collection and involved 5 brickand-mortar fashion boutique owner participants, who operated retail fashion businesses in the southeast region of the United States. The successful existence of the business for more than 5 years was an important prerequisite for participation criteria in the study, as also indicated merit in studying the critical success factors in traditional fashion retailing. The data from interviews were analyzed and triangulated with credible secondary sources such as information and reports from the U. S. Small Business Administration, U. S. Census Bureau, and the fashion industry. From a thematic analysis of the interview data, the major emergent themes were the importance of the business success of marketing strategies, cognizance of fashion trends and the role of customer preference in economic success resepectively. The ensuing knowledge from the utilization of the study may serve to increase the success rates of traditional and online fashion startups and possibly provide knowledge on the strategic imperatives for these businesses to compete in an online business world.