Luke Gillette stands between the racks at Simons in Mississauga, Ontario, on a mission to buy the tuxedo of his dreams.

Gillette said, "They have a crazy color I want to wear." "There's a pink suit here that I really hoped to find that matches my fiancée's dress, which is a blush pink."

Gillette is happy to support Canadian-owned businesses, but that's just one part of the retailer's appeal, as he said: "The selection is fantastic. The styles are modern, and the prices are really good."

The Canadian fashion and home goods retailer bets on happy customers like Gillette as it continues its gradual expansion. With 10 stores in Quebec and a handful of other locations spread between Vancouver, Edmonton, Calgary, and Halifax, the brand will open two locations in Toronto next year at Yorkdale Shopping Centre and Eaton Centre—along with stores in Mississauga and Ottawa.

However, as the company moves into a space haunted by the ghosts of major retailers past—Nordstrom, Eaton's, and Sears were all former tenants of Eaton Centre—it serves as a stark reminder that big-box stores have struggled to gain a foothold in the Canadian market.

The aforementioned brands (and Target) have faced their demise in this country over the past two decades, due to the challenges of transferring American businesses to Canada.

Even with rising costs, demanding customers, and online competition that’s roiling the unpredictable retail industry, Simons claims it is doing things differently. Can it overcome the curse of big retail?

"The reality is that we have to remain competitive."

Joseph Aversa, an assistant professor of retail management at Toronto Metropolitan University, said, "I wouldn’t say that... just because other big-box stores have failed in those places doesn’t necessarily mean that Simons will fail."

He pointed out, "Simons has faced a lot of challenges, right? In 2022 they encountered quite a bit of difficulty." The retailer was family-run until that year, when it appointed its first outside CEO, Bernard Lublan, to steer the company out of the shadow of the COVID-19 pandemic.

Aversa said that since then, the company has been “very deliberate in its expansions.” "It has grown relatively organically across the country."

Simons has seen steady growth in recent years following the end of the pandemic, according to CEO Lublan in an interview with CBC News, seeing a three percent increase in sales growth from 2022 to 2023.

But the executive is keenly aware of the challenges his predecessors faced in the Canadian market. He noted that retailers who succeed in a market suffering from failures are the ones who reinvent themselves by modernizing the customer experience.

Lublanck said, "This is what we are about... listening to our customers, ensuring that we are evolving, and that we are delivering what they expect."

While Simons stores in Toronto, Montreal, Quebec City, and Vancouver will have the same inventory, the company will adjust its offerings based on shopping behavior.

He says it is also trying to meet the needs of shoppers, whom he says range from younger teens to mature adults, by pairing high-quality fashion with reasonable prices. He acknowledged that whether this will resonate with the company’s expansion, remains to be seen.

"I think you will never know, right? The reality is that we need to keep our competitiveness. We need to listen to what customers are asking for. We need to continue to be obsessed with serving them and exceeding their expectations."

"The customer is changing"

Lisa Amelani, director and co-founder of Retail Strategy Group, said that Simons does a great job of designing its products to fit the tastes and sizes of customers, understanding their shopping habits both in-store and online, and having sales representatives who know the product well.

She noted that American retailers like Nordstrom made a grave mistake assuming that Canadians shop the way Americans do.

Amelani pointed out, "We are different. We are not just another state outside of the U.S., we are another country. And across Canada, we are completely different: the Vancouver customer is completely different from the Toronto customer."

She noted that the chain expanded very quickly in Canada, spreading thinly instead of investing in one or two key locations that could attract foot traffic—unlike the U.S., where Nordstrom locations cluster together. Other analysts noted that the chain overestimated how much Canadians would spend on luxury goods.

Amelani added that without a Canadian distribution center, Nordstrom was pulling stock from the United States—costing in shipping and fees—or from its Canadian stores, which meant its stores were low on certain styles or sizes.

Simons' main competitor, Hudson's Bay, has significantly reduced its footprint, announcing the closure of its Regina location after pulling out of Quebec, Alberta, Manitoba, and Ontario.

Amelani stated that Hudson's Bay has fallen behind the times and dropped the ball on the customer experience, "The customer is changing, but the store isn’t evolving with them."

Zellers stores are set to open inside 25 locations of The Bay across Canada

Amelani said that for a brand like Simons, there are other risks when expanding into the Canadian retail market.

She added, "We have so many options as consumers today. We have digital shopping, and we have Shein and Temu—both players in ultra-fast fashion," referring to the online Chinese retailers whose vast inventory and low prices have turned the industry upside down. She added that customers are also shopping on Instagram and other social media sites.

But she says she expects Simons to succeed in its expansion because it "has the trifecta—product, customers, and marketing. What they are doing is connecting all the dots."

"Unless there is another department store that will serve the needs of Generation X and Generation Z, we will see Simons thrive and succeed."