Harry Rosen's grandson speaks out on how the menswear empire is keeping up with customers following the death of its founder

With a loan worth nearly $6,000 today, a Grade 11 education and a seemingly irrepressible curiosity for tailoring, Harry Rosen launched one of Canada’s most well known menswear businesses out of a Cabbagetown storefront in 1954. By the time , Harry Rosen’s suits, shirts and other menswear had made their way to the wardrobes of movie stars, musicians and plenty of well heeled Canadian buyers.

The business had passed through three generations of Rosens (Harry’s son Larry Rosen is CEO, and grandsons Graham and Ian serve in executive roles). Harry Rosen sold suits before the Mad Men era began, and continues to sell them in spite of the . The latter might have killed it. A global pandemic is a trying time for a business predicated on exquisite attention to detail and a deeply personal relationship with customers.

Ecommerce, surprisingly, stepped into the fold. Over five years, online purchases at Harry Rosen jumped to 25 per cent from four per cent of all sales. Yet men’s fashion is a very different beast today from where it was when Harry Rosen first opened shop on Parliament Street in the 1950s. Suits are no longer in an office.

Nor are they confined to men. Many of the nuances of pocket squares or tie knots are no longer strictly observed. However, as Ian Rosen — the brand’s president and chief operating officer — told the Star, modern audiences are still keen on learning the code of men’s dress: Harry was incredibly giving with his original vision.

We watched him evolve the company so many times, including expanding beyond a single store to multiple stores. So Harry was no stranger to change. But every time we think about the next five years of the brand, we have the original vision Harry was building out. It had service at the core of it. It ensured we have a clear point of view on the fashion that a man might want to wear, and making sure that we’re the authority when it comes to clothing.

As you know, fashion has changed demonstrably since we’ve been in business. We turn 70 in a month. That vision continues in how Harry Rosen puts together what it’s doing. And it’s allowed us to retrench and focus in a number of ways. So Harry’s influence will never leave. That’s why his name is on the door.

Larry’s used Harry’s influence as a guiding principle. Graham and I, we’re the third generation of Rosens in the business, and we use it as a guiding principle. We’ve been reflecting on just how clear that vision was since Harry’s passing. Trying to figure out what resonates with the customer today isn’t the hard part.

Getting their attention is the hard part. We’ve rebooted the "Ask Harry" series. In the 1960s, Harry was putting together these incredible print ads that would position Harry himself as a menswear expert. "Ask Harry" would consist of questions like ‘where should my cuff sit on my dress shirt?’ ‘How much of my sleeve should be showing out of my suit jacket?’ ‘What tie knot should I wear to a specific event?’ It was very prescriptive, but it enforced, time and time again, that Harry was the expert when it came to menswear.

He would run this series almost weekly. It’s something that we’ve done for almost 70 years. We’ve been coming back to the "Ask Harry" campaign because we are menswear experts at our core, and younger customers are still looking for information — they’re just consuming it differently.

We actually partnered with an influencer on TikTok named Jack Innanen — we’ve put together a 16 video web series called "Ask Harry," about stuff like how to properly fold your dress shirt so it doesn’t look sloppy. I think that was probably our most successful one. Fashion cuts the market across two major spectrums, and there’s a fluidity that’s happening when it comes to styling and trends.

We made it pretty explicit in 2018 that if people don’t feel welcome — whether it’s a staff member or a customer — that’s on us. That was done to really combat the stereotype that a menswear store is an old boy’s club. We’ve been trying to fight against that from a cultural perspective.

There are collections that have been explicitly about attracting people to shop with us. I think Zegna is a really good example — that oversized, boxy streetwear look is attracting a lot of people. They’re one of our core vendors. In terms of servicing the needs on the women’s market, where body shape is different from what we’re used to, we’ve launched this quiet, made to measure program called Harold.

They have custom garments for women. I will say, we are staying true to Harry’s guidance here, which is to avoid doing something publicly until you’re perfect. We’ve been playing around with it. Our staff were really jealous of the fact we can make clothing packages now and really outfit our team to the nines — so we started with them, and asked ourselves how we can put together a garment that they want to wear comfortably to work five days a week.

But I think the core of your question is how you make anybody comfortable to shop at your store. That starts with the people that you’re hiring. We’ve seen a shift in the things that people are purchasing. Our suiting business hasn’t dropped, but if you actually look under the hood, it has become more formal and event driven, and a lot less about the four day suit wardrobe: two navy, two grey, and something fun.

People are getting a lot more expressive when they wear a suit. People want to wear something special. It’s going to be something that’s unique or different. Yes, there are industries where the dress code hasn’t changed. I love that. We’re making sure we’re a resource for them, but the categories that have spiked to compensate for that shift are what I would call "sports jackets and soft jackets," as a tailored piece on top of something a bit more casual.

Knitwear and sweaters have almost been the key to compensating against that shift, too. Men are looking for stuff that’s a little more casual forward. It’s not necessarily a dress shirt under a sports jacket. It’s a great polo, a great crewneck, or even a soft jacket that looks professional on a Zoom meeting — without involving a suit at home.

We talk to our staff about the "third layer." Someone has an undershirt, a knit piece and a layer on top — a vest, a sweater, a soft jacket. That third layer is really key to the way that men are dressing for work these days. We will enter any category where we can put forward a point of view, and where we can curate the best of what the market has to offer.

"What should I be wearing when I’m lounging around the house" has become a really great business for us. We’ve been in it for decades, actually, and I think we’ve expanded quite a bit. In the last few years, lounging at home has become more of a part of the way people live. As for things like activewear, we’ve never going to own the gym.

But we’ve also seen athletic wear cross pollinate into everyday wear. I use On running shoes as an example. They’re kind of the Silicon Valley staple — a guy wearing On Cloud shoes and a nice vest on top of a pair of jeans. So we’re making sure that we understand how a client is wearing specific things.

If we can curate it and become an expert, we’ll go into it. Even just from personal experience, it used to be super easy to get dressed. There was almost a uniform that was acceptable, and then there were things that were not acceptable. Right now, the world is your oyster, and I think a lot of men are counting on us to provide guidance to developing their personal style.

That’s really the future of our brand. We want to help individuals develop their personal style, and Harry’s original vision for the company was totally in sync with that..