Sears Canada began its operations as Simpsons-Sears Limited, a catalogue and mid-market suburban retailer that was a joint venture between the Robert Simpson Company Limited, a Canadian department store chain, and Sears, Roebuck and Company of the United States. In 1952, Sears Chairman General Robert E. Wood sent a letter to Simpsons President Edgar G. Burton, proposing a partnership between their two companies in order to serve the Canadian market. The deal to create Simpsons-Sears Limited, a Canadian catalogue and department store chain separate from the Simpson's chain, was signed on September 18, 1952. The new company would be a 50-50 partnership; Simpsons and Sears both invested $20 million and had equal representation on Simpsons-Sears' Board of Directors. The new company had two main objectives: to expand Simpson's mail order business (which was sold to the new company) and to build a string of stores modelled on Sears' format across the country.
The company made its public debut on the Toronto and Montreal stock exchanges on April 5, 1965, with the listing of its Class “A” non-voting shares. That year, Sears began its long-standing partnership with the Boys and Girls Clubs of Canada, to support its youth programming.
In 1972, Simpsons and Simpsons-Sears agreed to end the 25-mile restriction and permit Simpsons and Simpsons-Sears stores anywhere. The following year Simpsons-Sears opened a store in the city of Mississauga, approximately 30 km west of Toronto. To avoid confusing customers used to Simpsons, new stores were opened under the "Sears" banner. All existing Simpsons-Sears stores were rebranded to the Sears banner as well. However, the name of the company remained Simpsons-Sears Limited.
In 1974, Simpsons-Sears opened a Sears store at Hillcrest Mall in Richmond Hill, Ontario, its first location in a mall that had a Simpsons store.
Also in 1973, Sears achieved its first billion-dollar sales year.
In Canada, Sears continues to distribute their big-book catalogues, including the Wish Book. In 2012, Sears Canada chief Calvin McDonald hand-delivered Christmas catalogs to mark the 60th Anniversary of the Sears Wish Book.
'Nevada was Sears Canada’s main line of denim and casual wear for both children and adults. Introduced along with a revamp of apparel house brands in 1987. It followed in the footsteps of another long-popular but more utilitarian Sears jeans line, "Toughskins", which dominated in the 1970s. In 2013, Sears entered into a strategic alliance with Buffalo International Inc. to design and manufacture Sears' entire line of Nevada denim-based apparel (cited above).
In 2016, with the rollout of the Sears 2.0 concept, Sears Canada amalgamated most of its house brands into the Sears Woman, Sears Man, Sears Kids and Sears Home labels.
Sears tool line, like many of its other product lines, uses a "good, better, best" pricing structure, with the Craftsman brand as the middle tier and Craftsman Professional or Craftsman Industrial as the highest tier. The lower, value-priced tier was branded Sears. The "Dunlap" name was also used for from the late 1930s until the late 1950s. The Sears tool line was discontinued in the late 1980s and replaced by the "Companion" tool line. The Companion tool line was discontinued and replaced by the "Evolv'" tool line in 2008, with a focus on homeowners and do-it-yourselfers.
Among some of Sears house brands over time:
Sears Canada launched an iPad app for the 2013 Christmas Wish Book which is currently ranked as the number one free iPad app in Canada in the Catalogue category.
Sears Canada has received court approval to proceed with a full liquidation of its remaining stores, signalling the end of an era for a 65-year-old chain that was once a staple at malls across the country. Liquidation started Oct. 19 2017, and will continue for 10 to 14 weeks, stretching closing sales across the busy holiday shopping period.
Sears' wealthy uncle David Sears IV left him a significant inheritance. He used US$85,000 to start the Sears Foundation, which published the first Journal of Marine Research and the book Fishes of the Western North America.
Jessica was Sears Canada’s primary private label brand of women’s apparel and accessories, catering to the modern woman. It was introduced in 1987 and was the top-selling ladies’ fashion label in Canada.
Sears Canada and its predecessors were long been associated with its well-known house brands, each having a history of its own. For Canadian and overseas vendor suppliers, it maintained a Vendor Code of Conduct which, amongst other things, prohibits the use of child labour.
Attitude was a fashion-forward ladies’ fashion collection appealing to fashion conscious women. It had been an Eaton’s exclusive house brand and Sears continued the name. In 2010, when Canadian fashion designer Jay Manuel became its exclusive designer, the line became Attitude by Jay Manuel. Manuel also added a men’s dresswear line to the collection. In 2013, Sears entered into a strategic alliance with the ALDO Group to design and manufacture Sears entire line of Attitude and Nevada footwear for men and women.
Kenmore was Sears Canada's primary line of household appliances. The first Kenmore branded product was a washing machine marketed by Sears, Roebuck and Co. in 1927. The first Kenmore vacuum cleaners were sold in the U.S. in 1932. Simpsons-Sears began selling the Kenmore line in Canada in 1953. Kenmore's upscale line of appliances is known as the Elite line. Kenmore also has a professional line of appliances called Kenmore Pro. In the 1960s and 1970s, many housewares and personal electrics in the line were branded “Lady Kenmore” but its use was discontinued with the rise of sexism sensitivities.
'Coldspot was a Sears brand that existed from 1928 to 1976. The brand was created for a line of refrigerators. Other products sold under the Coldspot brand included freezers, dehumidifiers, and window air conditioning units. Sears, Roebuck had supplied this brand to Eaton’s for distribution in Canada, but the line switched it to Simpsons-Sears upon its founding.
In March 2009, Sears Holdings Corporation announced that it had purchased Delver.
The Sears catalog offered customers around the US a chance to wear "city clothes" throughout its 97-year-history.