Family business, reinvented: Tailoring a menswear brand to the digital age

When Ian Rosen joined his family’s business, Harry Rosen Inc., in 2018, he faced a daunting reality: Canada’s leading luxury menswear retailer had built its reputation on exceptional in-store service, but only a small fraction of sales — just 3-5% — came from e-commerce. In an industry undergoing rapid digital transformation, this was a significant vulnerability.

Then, the unthinkable happened. As COVID-19 forced all 18 of Harry Rosen’s retail stores to close, the company had no choice but to accelerate its digital transformation at an unprecedented speed.

But how do you modernize a legacy without losing the craftsmanship, service and personal touch that made it successful in the first place? That was the question Ian set out to answer.

A legacy of service, a future of innovation

Founded in Toronto in 1954 by Ian’s grandfather, Harry Rosen Inc. was built on more than just high-end menswear — it was built on relationships. “The big thing that my grandfather locked into early was that if he listened to the customer and wrote down a little bit about them, he could parrot it back next time and really take an interest in getting to know them,” Ian explained. “He built out this incredible Post-It note Rolodex. It was sort of a precursor to the modern-day CRM tool.”

That philosophy became the foundation for a modern, data-driven approach to client relationships. But first, Ian had to transform the company’s digital capabilities from the ground up.

Executing a digital overhaul

Ian’s first role at Harry Rosen was executive vice president of digital and corporate strategy—a new position that signaled the company’s commitment to reinvention. He approached the challenge methodically:

• Understanding the business first: Ian spent months immersing himself in the company’s operations before making any major changes. “It took probably six to eight months to understand, and then four months to pull together an informed recommendation,” he recalled.
• Building a scalable e-commerce foundation: By the end of 2019, just before the pandemic hit, Ian finalized the company’s digital software infrastructure partnerships. It was a complete overhaul of the company’s tech stack, a “scorched earth approach,” as he put it.
• Responding to crisis with speed: The digital strategy was well underway when COVID-19 shut down stores, and so there was no time for hesitation. “It wasn’t, ‘Let’s come up with a plan.’ It was, ‘Let’s start executing.’”

With that foundation in place, the company launched an entirely new e-commerce platform. The initial website was basic, and the team had a dogged focus on rapid iteration. “We had two or three quarters where we were releasing one or two features a week. And I think that was a great credibility builder,” he said.

Blending digital and personal service

The key to success wasn’t just launching an online store — it was integrating digital with Harry Rosen’s signature personalized service. Ian and his team developed an internal app, Herringbone, which allowed store advisors to build personalized webpages for clients and curate recommendations.

During the pandemic, this tool drove nearly 20% of online sales, proving that even in a digital world, human connection remained essential.

Reimagining the brand: “A life well dressed”

Since then, the company has continued to evolve. One major shift? Expanding its product offerings to better reflect changing menswear habits. “We try and bundle it under a new brand statement, which is:

Harry Rosen is for a life well dressed,” Ian said. While tailoring remains the company’s foundation — “like milk in the grocery store,” as Ian puts it — the real growth now comes from categories like casualwear, luxury leisurewear and sportswear.

This expanded range has helped the company fill its large-format retail spaces and resonate with a broader audience. “We had to find new ways to excite demand,” Ian noted. The team has also embraced a test-and-learn approach, trying new ideas and incorporating winners into their standard operating procedure.

A fresh take on brick-and-mortar

Alongside its product transformation, the company is in the midst of a sweeping physical redesign. Following a successful concept store pilot in 2024, Harry Rosen is updating its retail stores to reflect a more experiential approach. Think espresso bars, lounges and curated displays — not racks stacked with inventory.

“We’ve moved all of our suiting business into these amazing clothing areas we call the Kingdom of Clothing — a great place to buy a suit,” Ian said. “The rest of the store is about showing what else we do. There are lots of opportunities for our clients to get inspired.”

A new flagship store, set to open in Toronto in 2026, represents the pinnacle of this strategy. The new store will house two public floors, plus a private selling area to host VIP clients, with elevated client experiences throughout.

A new generation, a new era

While the company continues to invest in omnichannel innovation — with digital now making up roughly a quarter of the business — its greatest evolution may be in its leadership.

Ian now works alongside his brother Graham, who also joined the company and is now CFO. Together with their father, CEO Larry Rosen, they represent two active generations at the helm of the business. The family has embraced best practices in succession planning, governance and career pathing, partnering with advisors and implementing an independent board.

And in late 2023, the Rosen family marked a meaningful moment in their history: the passing of founder Harry Rosen. “We spent a year celebrating Harry in each market, which coincided with our 70th anniversary,” Ian said. “It was really special to see the whole country share their stories.”

Lessons for family business leaders

For family business leaders looking to drive transformation, Ian offers three key insights:

• Earn your credibility: When Rosen first joined the company, he didn’t hesitate to roll up his sleeves and dive in, even if that meant troubleshooting the website or handling customer service requests. “Especially carrying the last name of a founder, it was really important to me to demonstrate that there was no job or task that I didn’t want to understand.”
• Communicate relentlessly: Making sure that everyone in the company understands the big picture is difficult, but it’s essential. “You’d be surprised how few people are listening to that one town hall over Zoom that you did,” he said. You can’t overcommunicate the vision.
• Uphold core values: Employees should deeply understand those values and how they influence their work. “While online is a different channel, we still treat the customers who shop there as customers. We don’t want the online clients to feel less than.”

Looking ahead

Ian Rosen’s journey demonstrates that innovation and tradition don’t have to be at odds. By embracing technology, reimagining the customer experience and staying true to the brand’s core identity, he has helped future-proof Harry Rosen for a new era.

“For those who dislike change,” Ian likes to say, “you’re going to dislike irrelevance even more.”

For leaders of family enterprises, the challenge isn’t just staying relevant to the market — it’s ensuring the business remains meaningful to the next generation. Connect with the Ward Center for Family Enterprises at Kellogg to learn more about our resources and events for family businesses.