They sold the business for $135,000 in March 1898 to a syndicate of three Toronto businessmen, Harris Henry Fudger (1852–1930), Joseph Flavelle, and Alfred Ernest Ames (1866–1934).

In the 1960s, Simpson's was among the first 10 Canadian companies to start using computers in all their locations, and programming was done in Toronto and Montreal by accounting clerks, many of whom were women.

[11] The flagship store's acquisition of a large quantity of toy robots was a major plot point in the movie Short Circuit 2 in 1988.

Simpsons vanished from Greater Montreal in 1989 with its five stores either converted to The Bay or simply closed, leaving the chain with a presence only in the Toronto area.

[12] HBC acknowledged at the time that Simpsons wasn't doing great in Toronto but was still performing well enough to continue there and even planned to add three more locations to the existing 11 stores in the area.

[13] That year, the flagship Simpsons store in downtown Toronto completed a $30 million facelift with a relaunch known as the Miracle on Queen Street.

Its cosmetics area was reputed to be the largest in the world and the basement featured a gourmet food hall similar to Macy's in Herald Square in New York City or Harrods in London.

[12] The chain's operations in Greater Toronto were merged with The Bay in 1991 and the Simpsons name was retired after a retail presence of almost 120 years.

[4] Reasons for the Hudson's Bay Company's decision were the recession and the fact that it rarely made profits with the Simpsons stores ever since the acquisition in the late 1970s.

[11] Much of the operations of Simpsons and The Bay, such as purchasing, advertising and credit cards, had already been consolidated by the time HBC decided to merge the two chains.

[11] The Simpsons chain also suffered from an identity crisis within itself, with an upscale flagship downtown store filled with high-end merchandise in contrast to the mid-priced suburban mall locations that were basically like The Bay.

[11][14] When the merger was announced in June 1991, it had been suggested that the downtown location continue operating as a Simpsons store but HBC turned down the idea under the explanation that it would be too expensive to implement such plan.

[15] Finally, the demise of Simpsons came at a time when the Hudson's Bay Company was seriously controlling its operating costs in anticipation of an eventual entrance to Canada by American giant Wal-Mart which was already conquering the retail landscape in its country and attracting Canadians living close to the border.

[17] The locations that Sears acquired were closed in July 1991, renovated and progressively reopened at various dates in August and September 1991 with the former Simpsons/The Bay employees.

[27][28] The building later sat vacant for many years in the heart of the city's shopping district until it was turned in 1999 into a mall named Carrefour Industrielle Alliance, anchored by La Maison Simons and Famous Players (today Scotiabank Theatre).

The Canadian Intellectual Property Office database reports that the trademark to the name "Simpsons" was owned by Sears Canada from 2001 to 2008.

Designers in the St. Regis Room include Givenchy, Christian Lacroix, Valentino, Armani Collezioni, Louis Féraud, Karl Lagerfeld, Balmain, Andrew Gn, Lida Baday, Bellville Sassoon, David Hayes, and others.

Christian Dior, Oscar de la Renta, Yves Saint Laurent, Claude Montana, André Courrèges, and many others were featured in this luxury store.