In 1976, Smith founded his iconic WilliWear brand with his business partner Laurie Mallet. There, Smith continued to foster his ideas about dress, incorporating various inspirations that served as a vehicle for touching his audiences in personal and direct ways. For instance, South Asian dress primarily inspired Smith throughout his entire career, both before and after he established WilliWear. WilliWear collections — such as the one from Fall 1978, the more notable Spring 1974 City Island show, to a faction of the Fall 1985 collection — were inspired by South Asian dress elements like the salwar kameez, Jodhpurs, or choli bodices due to their ease, billowed silhouettes, and functionality. Smith wanted to create classic pieces that consumers could layer and remain trans-seasonal, which broke the industry’s trend-driven rules. He understood that most people were looking for clothes that gave them joy and complemented their varying body sizes while not having restrictive silhouettes.

Smith’s more personal inspirations for his design aesthetic were spurred by his ongoing journey of understanding his Blackness. Like many of his peers, he was triggered by the fashion industry’s incessant need to pigeonhole Black designers. He knew that his brand crossed cultural and color lines; thus, he did not want to feel suffocated by industry standards. Publicly leaning into his Blackness, for his Spring 1986 collection, many of the textiles and designs were an ode to West African dress. Even the motifs mirrored the glorious Bògòlanfini textiles native to the Malian region. In conjunction with the collection,  Smith produced a fashion film entitled Expedition, directed by Max Vadukul, which was filmed in Dakar, Senegal. He casted the film with locals and the Theatre National Daniel Sorano dance troupe, creating this fashionable dimension that celebrated a spectrum of Black culture behind and in front of the camera.

Smith was an incredible designer but an equally incredible multidisciplinary artist, collaborator, and entrepreneur. With United States workwear history serving as another inspiration to many of his collections, Smith extended this perspective beyond his showroom. In 1983 and 1985, Smith worked with his dear friends Christo and Jeanne-Claude to design uniforms for the workers assisting with the Surrounded Islands and Pont-Neuf Wrapped projects. Dance was an art form extremely close to Smith’s heart. He even enlisted Alvin Ailey dancers as models for the WilliWear Fall 1980 show to inject the scene with his signature mood of joy. Another costume designing effort Smith embarked upon includes his work on the 1984 Secret Pasturesperformance, choreographed by Bill T. Jones/Arnie Zane Dance Company with a designed set by Keith Haring and music composed by Peter Gordon. Smith’s costumes as well as many designs from external projects, including the patterns he created for Butterick and McCall’s throughout the 1970s and 1980s, reflected what he developed on the runway because to him, every aspect of his life was an effort to evoke a total work or a modern Gesamtkunstwerk.