Before she gained prominence as Mary Todd Lincoln's personal dressmaker, Elizabeth Keckley was an African American slave who bought her own freedom by way of her entrepreneurial pursuits initiated on the planation. Some writings detail Keckley's relationship with the first lady, less has focused on Keckley as a designer, dressmaker and entrepreneur. The purpose of this research was to learn from Keckley's words, artifacts and objects she created to understand her role and impact as an African American designer, dressmaker and entrepreneur. The study of Keckley's autobiography, artifacts, and photographs of garments she designed and constructed provide detailed insight into the work of a historical Black female entrepreneur who has mainly been known only as a personal dressmaker for Mrs. Lincoln and other affluent women during the antebellum period. This investigation of Keckley, through a Black feminist lens, provides a foundation for future studies of current Black female entrepreneurs in the apparel and textile industries.