Born in Speyside, Moray, Scotland in 1834, he was trained in the drapery trade before emigrating to Toronto, Canada at the age of 21 where he worked in a dry goods store. Before long, Simpson started up his own store and in 1872 he opened a pioneer department store in Toronto that eventually expanded into a major national chain.
In 1894, the company began issuing catalogues that are still produced today under the Sears (Sears-Roebuck) name. Originally the giant U.S. Sears company formed a partnership called Simpson-Sears but would later take over the complete operations.
Robert Simpson died in 1897 and is buried in Mount Pleasant Cemetery, Toronto.