In 1967, Smith left Parsons and pursued a career designing on his own. He first sought design inspiration from what people wore on the streets of New York. He befriended model
Bethann Hardison in 1967 after striking up a conversation about her style on the street. Hardison became the fit model for Smith's designs and a close friend. 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. The collection was a success, and soon after, Smith and Mallet formed the label WilliWear Ltd., with Mallet as President of the company and Willi Smith as Vice President and lead designer. The first Williwear fashion show was held at the
Holly Solomon Gallery in the Spring of 1978 and showcased a collection of garments “influenced by nautical uniforms and Southeast Asian dress.” WilliWear produced several hallmark collections from 1982 to 1986, and in 1986 the company reached $25 million in sales. Smith and Mallet further enriched the reputation of the brand through artist collaborations. After Smith's death, on April 17, 1987, Mallet continued to run WilliWear. In 1989, Mallet hired designer
Andre Walker to revive the brand. Following a poorly received Fall 1990 collection and loss of sales at the Fifth Avenue store, Williwear filed for
Chapter 11 bankruptcy and ceased production in 1990. == Collaborations ==