Man About Town: Town Shoes founder Leonard Simpson

Yvonne Palkowski
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When Leonard Simpson (BA 1950 UC) opened his first shoe store at the age of twenty-two, he could not have predicted that the operation would grow into Canada’s largest branded shoe retailer, including Town Shoes, The Shoe Company, Sketchers, Freedman, Shoe Warehouse, and Sterling.  “I didn’t know a thing about the shoe business,” says the charming and affable Simpson, now 84.  He came to be known for creative business decisions, from pioneering the strip mall retail concept, to sponsoring Toronto Fashion Week for an impressive 25 seasons. While he sold Town Shoes shortly before its sixtieth anniversary last year, Simpson remains involved as  honorary chair—you could say he is the ‘sole’ of the business. He spoke with UC Magazine editor Yvonne Palkowski about the business side of shoes.


How did you turn Town Shoes into the largest footwear retailer in Canada?

My father was in the wholesale shoe business, he owned three stores. He wanted me to go into his business after I graduated but I didn’t want to, so he asked me to at least look at the stores and make suggestions. I advised him to get out of those stores because they were losing so much money and they were terribly run.  Then he asked me to sell the stores, which I did. I sold two stores in a week. I was only 22 years old.

As for the third store, I was running it while looking for a buyer when my good friend Avie Bennett (1950 UC) said his parents were opening a shopping centre. I asked him what a shopping centre was—this is 1952. He said it was a strip mall called Sunnybrook Plaza, with 14 stores and a small parking lot. I thought it was a very, very good idea. You have to understand, it was the very first concept of that nature in the entire country. I went to my dad and asked to use the proceeds from the sale of the third store to open a retail store at Sunnybrook Plaza, at the northeast corner of Eglinton and Bayview in Toronto. It turned out to be reasonably successful.

Then Avie said they were opening up another shopping centre, a bigger one at Lawrence and Bathurst called Lawrence Plaza. To make a long story short, I sold the first store to finance the opening of the second store, which turned out to be a bonanza. I did a huge amount of business, and the cash flow from that was the beginning of the rest of the stores. I never borrowed a nickel after that from anybody (except for the usual financing from the bank to turn over inventory). That’s how it started.


You studied political science and economics at University College. How did your education play into your career?

You know what I learned most at University? Are you ready for this? How to play bridge. There was a lot of playing bridge, five days a week after first year. Except, of course, for the month or so before exams, when you worked your butt off. I learned a lot playing bridge, it’s a good brain game.

An education is always useful, but did it have a direct effect? Indirectly, probably. If I hadn’t gone to University, I could have possibly done the same thing. Drive, motivation, and aptitude has more to do with it than anything.


Describe the thinking behind the new line of stores you’re opening this year.

What is happening with everything in the apparel industry is the upscale people, in order to get volume, are creating brands aimed at younger customers – Kenneth Cole has Kenneth Cole Reaction, Steve Madden has Steve Madden Girl. The young market, like everyone else, likes brands.

We’re working on creating a division of stores with the cachet of Town Shoes but aimed at a younger market. The concept is to sell shoes in a similar price bracket as Aldo, the global leader in young shoes, although instead of private label, which they do, ours would be branded young shoes, essentially.

Will we seriously compete with Aldo, globally? I doubt that very much. Domestically, within Canada, we’ll see. It’s not something that’s going to happen within a short period of time, but in the long term, probably after I’m gone, who knows. Aldo is good at what they do, but they have no competition. With the experience we have, the buyers we have, and the knowledge we have, we may just have something.


What are the upcoming trends in footwear?

 In addition to classic fashion, which is what we like to do, we also have to do ‘bling’ shoes because that attracts a lot of customers. But you have to be careful on the weighting between classic and bling, because if you have too much bling, you scare away the classic fashion customers and vice versa.  Town Shoes captures the best of both worlds by continually adjusting that balance. Right now we’re in the process of reducing the ratio of bling to classic fashion and there’s a reason for that: people are becoming a little bit more practical, a little bit more down-to- earth. People don’t want to spend $700 on a pair of shoes they’re going to wear once or twice, or for a season or two. They want something with a style that will hang around for a while, and where the look is going to be useful for a variety of different purposes.

There’s also a huge trend toward developing fashionable comfort shoes.  The casual look is taking over. For every men’s leather-soled dress shoe we sell, we sell about nine or ten casual shoes. Women still wear more dress shoes than men, but the ratio has gone way over to casual. Wedges are starting to take over from heels for office girls—they’re still wearing heels, but there’s a trend towards wedges and ballerina flats. There’s a trend towards comfort, softness, and cushiness in shoes. People want that kind of feel in a casual shoe, even people who are younger and middle-aged, not just people who are older. That’s probably the biggest trend in the industry today.


What do you think is driving that trend?

It’s a practicality, a rationality that makes sense. People also want to buy cars today that don’t burn too much gas—it’s the same idea. When people wear shoes that don’t feel good, after a while, they’ve had enough. We’ve been there, and it takes a couple of generations for attitudes to change.


There are a lot of self-described shoe addicts out there. What is it about shoes that excites people?

It’s funny, I went to get my iPhone a few months ago, and the young lady behind the cash asked what company I was with. I said Town Shoes, and she became very excited and asked me what I do there. I said I happen to be the founder. She pulled out a pen and asked me for my autograph!

There is something about shoes; I don’t know what it is. They’re something we all wear... And you can really tell what a person is like by the kind of shoes they are wearing.