He is not only executive chairman of “Harry Rosen Inc.”, which operates a chain of 16 menswear stores in the eight major markets in Canada, but also a Canadian icon. This fact, in and of itself, is a remarkable accomplishment for a Canadian clothier – and a case study in marketing done right. In 1961, Harry Rosen vaulted into public consciousness with the “Ask Harry” ad campaign, and instantly became both the face, and embodiment, of what would become a retail empire.

In 2005, Rosen stepped back from day-to-day management of the company and now advises his son, chairman and CEO Larry Rosen. It’s been a smooth and productive transition, with Larry spearheading the launch of the newly renovated flagship store in downtown Toronto, the largest menswear store in Canada.

Despite turning over the helm to his son, Harry Rosen remains vital and involved, serving on prestigious boards, actively fund-raising, and writing and delivering retail management training programs.

TORO recently caught up with the innovative and forward-thinking Rosen for a discussion about his own sense of style, style versus fashion, and the key to his clothing empire’s longevity and success.

Q: How would you describe your own personal sense of style?
A: I have a great deal of confidence in putting myself together. And I think I’m perceived by people, well, to not be fashion forward – I never have been. I tend to be on the traditional or classic side of the fashion spectrum, but still making a contemporary statement. It’s me. At the same time I know the era I’m living in and I hope to never date myself by living in the past. My clothing is sufficiently modern to be seen as someone who is in touch with what’s going on in today’s world.

Q: Can a man by stylish without necessarily being fashionable?
A: Yes, yes he can. There are people that I call frivolous spenders, always indulging themselves in the latest things. They’re fashionistas. I have never been a fashionista. I’ve never chased fashion. I’ve always dressed in a way that makes me feel confident and I think makes me be seen the way I want to be seen. I think of fashion as being ephemeral – it’s thin, it’s veneer. I think there should be more substance to the way one dresses.

When I dress people I have a sense of how far into the contemporary era they want to be. I can serve a young customer, and understand a young man, in a substantive sort of way. Young men begin to take clothing seriously when they come out of university and are launching themselves into a business career. Up until then, their approach to dressing properly is more passive. But I know that it’s an important stage in their lives, and I get a sense of how they want to position themselves after talking to them.

Q: When it comes to men and dressing well, isn’t it all about engendering confidence?
A: I think behind it all is a matter of gratification. Confidence and feeling good about yourself is important. And I want that to emanate from my customers.

Q: What’s the cornerstone of a great wardrobe – the essentials that every man should have.
A: Well, it depends where they are on the spectrum. For instance, there’s the corporate type – lawyers, entrepreneurs, or those in the IT business. By the way, so many people in the IT business, and even young lawyers and other professionals, when they try to dress casually end up looking like they just don’t care. Now you can be appropriately dressed even if you are sitting at a computer all day, because you still need to feel good about yourself.

Corporate is one lifestyle. The first suit a corporate guy should own is a dark suit, just like you have on. And the plainer, likely, the better. Yours is a good suit and it probably has a good life in it. It’s plain – except it’s got a little window pane check. But it’s not obnoxious, not something that would draw attention to itself. It’s quite distinctive, actually. It certainly serves well as a dark suit.

The corporate type needs a dark suit – and he should have a couple of them. And if he’s a shirt and tie guy – though a lot of men dress like you are now, with an open neck, and that’s quite acceptable – but if he’s a shirt and tie wearer then he needs several shirts and several ties, because that’s where you create interest in that dark suit. You change it by virtue of the accessories. A lot of men don’t know how to do that. Now you’ve got a nice light blue shirt on. That’s good. But now and again a nice stripe or a check is a nice alternative and it keeps people thinking that you’re an interesting person.

Now if you are sitting at a computer, or you have limited interaction with the public, then you can still dress in a casual way that still suggests that you’re a thinking person and still have some respect for your appearance. And what I’m saying about the corporate people who dress down, either occasionally or on an ongoing basis, is that they’re so absolutely boring, they are so much a part of the wash, that they just do not distinguish themselves. Now I don’t think clothing makes the man, but I think it helps – it’s part of the glue that holds him together. And right off the bat, when I see the corporate types who dress in an offhand manner, I think, “Well, they sure aren’t progressive looking. Are they progressive?” And maybe they are. But I’d have to discover that through our discussions, not through initial impressions.

Q: I suppose the challenge is to be able to dress down without losing all sense of elegance and sophistication. I think the Europeans do that well – the Italians, the French.
A: Make a statement. I was at a meeting hosted by a large number of lawyers from a downtown firm. Now, based solely on the way they were dressed, I didn’t know if they were members of the firm or if they were there to clean up after we left. They were dressed in such a boring manner, just so completely uninteresting, but then when we got to talking, I found out they were involved in fascinating areas – technology law, entertainment law. They were really interesting people. But you wouldn’t have thought that from looking at them.

Q: I can picture what a well-dressed Italian would look like. A British guy too. Even a fashionable but busy New Yorker. But is there a similarly distinctive look for the Canadian man?
A: Years ago I’d have less trouble giving you that explanation. I saw Canada as positioned somewhere between England and the United States. And the look that the United States projected internationally was shorter pairs of trousers and soft shoulders. English guys were dressed in waisted jackets and full chests, and that was the very elegant era of the ’30s. Canadians were somewhere in between, not as relaxed as Americans but not as stodgy as the Brits. Today there is such an international flavour to fashion. If you go to New York and you go to Toronto, and hit the stores that are alive and with it, like our Bloor Street stores, there’s nothing to distinguish Canadians apart from the Americans or British. Zegna sells in all these places. Canali too. The only place I see a real variation is in Italy, where they still have some things about the way they dress that is particularly Italian. And that is that their trousers are closer fitting, and their jackets a bit shorter. But, despite that, there is really an international flavour to fashion today.

Q: When you look back to all the different eras, and the men’s fashion and style embodied by each – the post-war look, the elegant style of the ’30s – is there that has a particular resonance for you?
A: Gregory Peck dressed in a three-button suit with narrow lapels and soft shoulders and plain front trousers. And I’d have to distinguish between that and what the Rat Pack were known to wear, later on, and that was short jackets with side vents and a little more shoulder expressions, and that came out of the entry of European clothing starting to make its way into our culture.

The look that I describe Gregory Peck wearing was authentically American. It was not Saville Row. Like I have on right now, actually, though not quite as progressive as this.

Q: Now if you were to have one outfit that you feel best in, is it wearing a nice suit?
A: No. In the last year, I have taken more holidays – and I’m in leisure clothing much more, I very seldom wear a tie, and wear jeans and sport shirts (but with a little character to them) and most of this is interchangeable, but it’s all in good taste – at least in my opinion. And always, in my case, with some sort of jacket – a soft, unstructured jacket that probably doesn’t weigh more than a sports shirt, but it’s somewhere I can put all my junk. It’s a great utilitarian item. I have a navy blazer in cashmere for fall and I have it in linen for summer. I give it a lot of wear, the blazer.

Q: Harry Rosen just launched a newly renovated, almost 50,000 square foot, five-storey flagship store in downtown Toronto. Can you look back and reflect on the success and longevity of the company, especially as it all started in a single room store on Parliament Street.
A: I started out doing it all – the buying, the selling, every aspect of retailing in a small business. I thought business all the time, and I applied myself, and had the gratification of being able to measure my learning and where I was at through the referrals of existing clients. I earned my referrals. And that was the building of a reputation.

I took those same standards, even when I started to delegate, my sense of mission and what we were about, and I built an organization based on people who share that vision. And as the business grew I was always very concerned that the span of this growth would dissipate the quality of the service that I aspired to. Because it never changed from being that small operator to sharing it with several hundred people.

You never rest on your laurels, you never rest on your past achievements, because there’s always some other guy that’s going to compete with you who’ll be fresh and small and hungry, and they’ll do things that are outside of your approach. And there’s room for them. If somebody comes in with a new idea, they should be successful. The only thing is that I want to be aware that they are there, and I want to take what I can from that lesson and incorporate it into our business. And that’s how you stay young.

William Morassutti is the co-founder and Executive Producer of He was one of the founding members of TORO Magazine, where he served as both Editorial Director and Executive Director. Prior to joining TORO, he worked in Canadian broadcasting as a writer, producer, director, reporter and host.