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"This has become a great introduction to that new way of dressing," Rosen said, motioning to rows of the same T-shirt now sold in almost a dozen colours at Harry Rosen's store in the tony Yorkville neighbourhood.

"It's very modern. It's very approachable."

That vibe is exactly the one his family business is aiming for as it celebrates 70 years since its namesake Harry, who died in December at 92, and his brother Lou opened a small, made-to-measure menswear store in Toronto's Cabbagetown with a down payment of $500.

The luxury business has since cemented a reputation for being the epitome of haberdashery, but these days, president and chief operating officer Ian Rosen says it's on the brink of reinvention.

The company is pouring $50 million into renovations meant to update its 14 stores and five outlets. It will also move the marquee Bloor Street West location Rosen was recently strolling around the corner to Cumberland Avenue, where shoppers will be treated to a patio overlooking Yorkville, a client lounge, an espresso bar and valet parking on weekends.

The brick-and-mortar changes will freshen up the brand's footprint, boost its customer service and more importantly, help Harry Rosen address a larger challenge: the evolution in men's style.

"The old wardrobe used to be two blue suits, two grey suits, a number of dress shirts, a number of ties, and you could make infinite outfits out of that and that was your work wardrobe. Then, you had a weekend wardrobe, which you didn't really invest in that much," recalled Ian Rosen, clad in a beige golf shirt and navy blazer.

"Today's man's wardrobe is really dressing for your day. It's about putting yourself together much differently for the workplace."

That evolution — noticed years ago by Ian but accelerated in part by the COVID-19 pandemic — means men are playing with denim, vests, outerwear and jackets with "soft," or unstructured, shoulders.

They're not afraid to blend fancier pieces with more relaxed staples to create a "dressy casual" look, he said.

While Harry Rosen is still a go-to for dapper suits, bow ties and fancy footwear, a mannequin donning a sport jacket and light-washed jeans is not out of place now. Nor are racks of $1,195 Brunello Cucinelli shirts carrying an "easy fit" or a Canada Goose department selling belt bags, jogger pants and hooded sweatshirts.

Revamping the product assortment is an admission of the changing times but to make it work, Harry Rosen has to strike a balance, said Lanita Layton, a luxury and retail consultant who was once a vice-president at Holt Renfrew.

"They don't want to lose their older customer, but they recognized they need to bring in that younger fellow now," she said.

One might think the company's namesake would have scoffed at the shift, but Ian Rosen said his grandfather "never turned his nose at change."

"He was impressed with how people are bringing what he called 'sartorial elements' into casual wear," Ian Rosen recalled.

Every week, the pair walked through at least one store, chatting about trends in menswear and consumer habits, but it was never a given Ian would join his grandfather and CEO father Larry in helping the family business navigate the current evolution in men's fashion.

"I wanted to go figure out my own thing," Ian said.

For much of his career, Ian worked in management consulting, mostly helping grocery, apparel and consumer goods companies with their e-commerce strategies.

The businesses had a lot of parallels with Harry Rosen, which Ian said had made a lot of "base-level investments" in e-commerce but "hadn't really gone for it."

Recognizing the synergies in his son's work and his own business, Larry invited Ian to come up with an e-commerce plan for Harry Rosen.

"I joined in 2018, and I feel like my foot's been on the gas pedal ever since," Ian said.

So far, he's had to navigate the COVID-19 pandemic, which scuttled demand for exactly the kind of attire Harry Rosen specializes in. Ian said the crisis arrived at "the worst time" as the March through July period includes the busy wedding season.

Despite the health crisis, consulting firm McKinsey & Co. concluded the luxury market grew, but it was not unscathed. Department store (and Harry Rosen rival) Nordstrom, for example, fled Canada last summer because of profitability challenges. McKinsey predicted growth across the entire luxury market would slow as even the wealthiest shoppers felt the effects of an economic downturn.

"Between interest rates and mortgage rates and the price of other things, it's definitely making the client more discerning with their dollars," Ian said.

Yet many customers are still willing to spend, especially through Harry Rosen's e-commerce channels, which have grown so much that Ian Rosen says "online is our biggest store."

He's found shoppers order a pair of shoes or a shirt they already have in another colour from their couch, but take an informed yet exploratory tack when they visit stores. They come in armed with intel gleaned from online searches but are looking for inspiration or to shop for an entire season at once.

"The customers in luxury, especially, do their homework," said Layton. "That's where the digitization is so key."

Noticing this, Ian launched Herringbone, a tool named after his favourite print that sales associates can use to look up inventory and client information and build pages of curated products for individual shoppers.

The merchandise they can choose from these days stretches well beyond apparel. Harry Rosen now stocks grooming products like beard oils, toothpaste and deodorant along with decor, stationery, books and kitchenware.

Ian sees the additions as a logical extension of Harry Rosen's core strength — curation — which his grandfather developed by travelling the world in search of the best of the best for shoppers.

"We're not trying to be in the furniture business," Ian said. "We're not trying to provide people with something that they could get down the road."

The company's rationale is sound but the more they branch out, the more likely they are to run into additional competitors, Layton said.

Holt Renfrew and Hudson's Bay have long been Harry Rosen's biggest rivals, but designers have increasingly opened their own shops, and custom suit business Indochino often goes head-to-head with the company's made-to-order label Harold, which recently started a womenswear pilot.

Harry Rosen's broader range of merchandise also puts the firm in the same territory as independent boutiques and specialty retailers like Indigo Books & Music Inc. and Williams Sonoma.

"Harry Rosen will say that everybody's their competitor, and I would probably echo them on that," Layton said. "They look at the world. They never look at just Canada."

That approach is apparent as Ian Rosen points out highlights of the Bloor store. There's a department for Ralph Lauren and an area dedicated to Maurizio Baldassari, the Milanese brand whose second generation he is "super close" with.

Reflecting on the longevity of his own company, he describes Harry Rosen as "lucky" to have reached 70, especially when he considers that only 12 per cent of family businesses make it to a third generation.

Though succession planning is likely far from Harry Rosen's top priority with Larry at the helm, Ian as second-in-command and his brother Graham running the outlet business, one can already see a glimpse of the potential future.

When Harry Rosen died, he had nine grandchildren and six great-grandchildren, four of them Ian's daughters, who are all under the age of five.

"I was trying to explain to my daughter this morning what I did. She was not fully processing it," Ian said. "But they love the mannequins."

This report by ºÃÉ«tvwas first published Sept. 23, 2024.