Winston Kong was born in Ipswich, Jamaica. He studied at Cornell university and planned to go into hotel management before realizing his passion lay in the fashion world. After attending the Fashion Institute of Technology, Kong worked for Henri Bendel in New York for a year before taking a job in March, 1963 designing dresses for Mr. Smith, a Toronto boutique manufacturer. In 1966, Kong set up his own couture business on Gerard street, which he moved to 158 Cumberland Street in Yorkville in 1970.
Known for his exuberant party clothes, most often made in silk taffeta, Kong created for clients who attended Toronto social events like the Sunnybrook Hospital ball, Opera ball, and Art Gallery ball. He would make no more than four of any of his designs, but even then, each would be different because they were all made on the premises for the client, rather than at a factory from a master pattern. Kong did eventually learn to carry a small selection of ready-made dresses for last minute shoppers who needed something for an event the same day. In the 1980s, his creations, which were similar in style to designs by Valentino and Ungaro, sold for between $900 and $1,400 each. Kong closed his shop in about 1995 and died in 2005.