By CanadianJeweller.com and inspired by LeeAnn Shelton|Kellogg School of Management
In the Canadian luxury retail landscape, few names evoke heritage and craftsmanship quite like Harry Rosen Inc. Founded in 1954, the brand grew from a single Toronto storefront into a dominant national force in menswear. For decades, the business was synonymous with tailored suits, five-star service, and generational customer relationships.
But by the late 2010s, it faced a stark truth: legacy alone wouldn’t carry it through a digital age.
Enter Ian Rosen — grandson of founder Harry Rosen, Harvard MBA, and former management consultant — who joined the company in 2018 with a singular focus: evolution.
Today, as President and COO, Ian is not only steering the brand through an increasingly digital marketplace, he’s redefining what it means to run a multi-generational, customer-centric luxury business in a world where convenience often trumps loyalty.
And he’s doing it without losing the soul of what made Harry Rosen iconic in the first place.
The Urgency of Digital
In 2018, less than 5% of Harry Rosen’s total sales came from e-commerce. “We had exceptional brick-and-mortar service — but digitally, we weren’t where we needed to be,” Rosen told Kellogg alumni in a recent spotlight feature.
That vulnerability turned into a full-blown crisis when COVID-19 shut down all 18 stores across Canada. Overnight, Rosen’s digital transformation plan went from roadmap to lifeline.
Instead of scrambling, the company executed. With foundational work already in place — a full tech stack overhaul and scalable e-commerce architecture — the team rolled out a new online platform in weeks, not months.
“We went from ‘strategy’ to ‘execution’ instantly,” Rosen recalls. “There wasn’t time to talk about what the future looked like. The future was now.”
Where Legacy Meets UX
What made the digital shift so unique wasn’t just the rapid implementation — it was the deliberate preservation of the Harry Rosen experience online.
That ethos dates back to the company’s earliest days. Founder Harry Rosen kept a handwritten Rolodex of customer notes — everything from favourite brands to birthdays — to deliver more personal service. Decades later, Ian Rosen’s team developed Herringbone, an in-house platform that lets store advisors curate personalized digital storefronts for individual clients.
At the height of pandemic lockdowns, Herringbone drove nearly 20% of online sales. “Even in e-commerce, customers still want to feel seen,” Rosen says. “Technology should amplify that, not erase it.”
That integration of humanity and tech now defines the Harry Rosen omnichannel experience — and it’s paid off. Digital sales today make up close to 25% of revenue and are growing.
“A Life Well Dressed”: Rebranding for the Hybrid Man
Beyond technology, Rosen understood the brand itself had to evolve. Post-pandemic life shifted how men dressed. The tailored suit — once the bedrock of the business — was no longer a daily essential for many professionals.
So, the brand repositioned itself. The new brand promise? A life well dressed.
“It’s not about abandoning tailoring,” Rosen explains. “It’s about expanding what style means for today’s man — from the boardroom to the brunch table.”
Categories like luxury leisurewear, hybrid workwear, and designer sneakers now sit beside Zegna and Canali. The product mix became more fluid, curated, and reflective of lifestyle realities, all while maintaining the premium quality and service Harry Rosen customers expect.
Physical Retail, Reimagined
While e-commerce became a pillar of growth, Rosen hasn’t turned away from physical stores — he’s reimagined them. In 2024, the company piloted a new store concept that blends retail with hospitality: espresso bars, lounges, curated vignettes, and reduced inventory on the floor.
The idea: turn stores into spaces of inspiration and conversation, not just transactions.
“We moved all of our suiting into what we call the Kingdom of Clothing,” Rosen says. “And the rest of the store? It’s where we spark desire. It’s where style starts.”
The new flagship store, set to open in Toronto in 2026, will feature two levels of curated public space, private VIP lounges, and digitally connected touchpoints throughout. It’s not just a store — it’s a brand statement.
The Next Generation of Family Leadership
Of course, this reinvention isn’t just operational — it’s generational. Ian now shares leadership duties with his brother Graham Rosen, CFO, alongside their father, CEO Larry Rosen. Together, they’ve built a governance structure rare for family-owned retailers: an independent board, clear succession planning, and defined executive pathways.
The transition wasn’t accidental. The Rosen family spent years working with advisors, professionalizing the business without corporate dilution.
In 2023, the family also marked the passing of founder Harry Rosen, celebrating the brand’s 70th anniversary with national campaigns that honoured its roots. “The stories we heard from customers across the country reminded us why this brand matters,” Ian says.
Lessons for Retailers — and Family Enterprises
For Canadian retailers, particularly those with legacy models, Harry Rosen’s evolution offers more than inspiration — it offers a roadmap.
First, leadership must be earned, not inherited. Ian Rosen spent months in operational trenches before making any strategic recommendations. From customer support tickets to backend logistics, he immersed himself in every detail.
Second, overcommunication is essential in periods of change. “Don’t assume a single town hall or Slack post gets your message across,” Rosen says. “Repeat the vision. Then repeat it again.”
Third, values are your compass. Even with a digital focus, the Harry Rosen team remains committed to its founding principles: impeccable service, trust, and customer relationships.
“For us, online customers aren’t separate — they’re just shopping through a different door,” Rosen says.
In conclusion
Harry Rosen Inc. is a case study in retail reinvention: a legacy brand that embraced change without compromising its core identity. Its story speaks to every Canadian business grappling with disruption, every family enterprise navigating succession, and every luxury retailer redefining relevance.
In a world where attention is fleeting and loyalty is fragile, the company’s success is grounded in something timeless: knowing who you are, and having the courage to evolve anyway.
As Rosen puts it, “For those who dislike change, you’ll dislike irrelevance even more.”
