From 1969 to 1973, Smith worked as lead designer for the junior sportswear label Digits. Smith met future business partner and lifelong friend Laurie Mallet in 1970 while Mallet was in New York for a holiday break and hired her as his design assistant at Digits in 1971. The following year, 1972, Smith was nominated for the Coty American Fashion Critics’ Award for his work as lead designer at Digits. In 1973, Smith was nominated for the Coty American Fashion Critics’ Winnie Award for the second time, and began designing patterns for the commercial pattern company Butterick. Smith resigned from Digits later that same year and Digits went bankrupt shortly after. In 1974, Smith partnered with his sister Toukie Smith and close friend Harrison Rivera-Terreaux to form his own label Willi Smith Designs, Inc. Unfamiliar at the time with the business aspect of running a label, the company struggled and closed a few months later.