Canadian menswear titan Harry Rosen, pictured inside his Toronto office on Oct. 19, 2016, opened his first store in Toronto’s Cabbagetown district and went on to build a nationwide menswear business in the decades that followed.Christopher Katsarov/The Canadian Press
Harry Rosen’s ad campaign, Ask Harry, has run on and off for more than 60 years. The ads answer questions about the finer points of men’s fashion, such as how wide cuffs should be on trousers and how much of a shirt sleeve should show at the wrist of a sports jacket or suit.
The idea came from an advertising executive who walked into Harry Rosen’s clothing store in the early 1960s. “I’ll write the ads and you pay me by giving me two suits,” adman Stan Berkoff said. This was the beginning of his long relationship with Mr. Rosen, who died on Dec. 24 at 92.
Harry Rosen was born in Toronto on Aug. 27, 1931. His father, Abe, was in the scrap metal business, his mother, Sarah (née Baumel) was a housewife. Harry went to Harbord Collegiate then started to work at a clothing store on Bloor Street run by a man named Sam Lebo, who later would end up working in a Harry Rosen store. The teenage Harry Rosen fell in love with fashion and helping men pick what to wear.
Soon he went out on his own. Mr. Rosen borrowed $500 and opened his first store in Toronto’s Cabbagetown district, long before the area became fashionable.
“In 1954 I heard about a new men’s clothing store opening on Parliament Street. I was very interested in fashion and wanted to see what this new store had to offer,” Gary Sneedon said. He had low-paid job on the floor of the Toronto Stock Exchange and got a part-time job at the new Harry Rosen clothing store.
“I like to say that I was Harry’s first employee,” Mr. Sneedon said. “I enjoyed my time working with Harry, he treated me like one of the family. He even invited my girlfriend, who later became my wife, and me over to his house for dinner.” Later Mr. Sneedon left to work in the brokerage business full-time and switched from employee to customer. “I was a customer of Harry Rosen for many years and have never lost my passion for men’s fashion.”
The $500 loan wasn’t enough for a lot of inventory, so the shelves were filled with many borrowed empty boxes with brand names and some swatches of cloth. Harry and his brother Lou got into the made-to-measure business. Take the measurements, send them to a shop to get made and you have a successful tailoring business.
Mr. Rosen dealt with Coppley Apparel in Hamilton, whose main brand was Cambridge. At first, he would buy off-the-rack jackets and suits from them, then he would take measurements and send the details to the factory which would send back custom-made jackets and suits.
Harry Rosen’s Ask Harry ad campaign has run on and off for more than 60 years.
“Harry was all about bespoke,” said George Lindsay, the former president of sales at Coppley. “Harry thought everyone on the face of the earth should be wearing made-to-measure.”
Mr. Lindsay said Mr. Rosen was amazing with customers.
“I would watch him with people in the store when I visited. He treated everyone the same, whether they were buying a custom-made suit or just shopping for the first time. It was a fantastic thing to see.”
One customer remembered getting the Harry treatment when he wandered into the store on Bloor Street and Mr. Rosen happened to be there.
“He recognized me from our workout club. I had a BlackBerry on my belt. Harry took a chalk and marked up the jacket in a way that it looked good with the BlackBerry, then turned it over to one of his tailors. I still wear the jacket,” Peter Rehak said.
“Harry was an entrepreneur who willed the business into existence through his determination and passion,” said his son Larry Rosen, a lawyer who joined his father’s firm in 1985 and is today the company’s chairman and CEO.
In the mid-1950s, Toronto men dressed in a conservative, British style. Jackets had padded shoulders and a cut that hadn’t changed for decades. Harry Rosen changed that.
Throughout his life, Mr. Rosen liked to travel and always looked to see what men’s clothing stores were doing in other cities and countries. In 1957 he went to New York and was blown away by a new look worn by the young advertising executives of Madison Avenue and others, immortalized in the movie The Man in The Gray Flannel Suit and by the well-dressed stars of the television series Mad Men.
“Harry bought a natural-shoulder garment in New York City and brought it back to Toronto and took it to his made-to-measure factory and said, “I want this look and I want my made-to-measure to be in this look,” Larry said. “That cut was so novel in Toronto and all the young executives wanted that Harry Rosen look.”
Mr. Rosen then went to where the money was: Bay Street in Toronto’s downtown financial district where in 1961 he opened a store on Richmond Street between Bay and York. It happened to be across the street from the Cambridge Club, a squash and workout gym and Mr. Rosen drifted over and got into running.
“Harry became a member of the early morning fitness and running group,” says Clive Caldwell who started as the club’s squash pro and now owns a few downtown workout clubs. Mr. Caldwell was also a Harry Rosen customer. “Harry made a made-to-measure tuxedo for my wedding 17 years ago.”
It was around the time of the move that the Ask Harry ads started running.
In 1968, Mr. Rosen was approached by the Wilfrid Posluns who ran a chain of fashion stores under the Dylex banner. Mr. Posluns bought 100 per cent of the Harry Rosen chain and Mr. Rosen began running all the men’s wear operations of Dylex including its Tip Top Tailors factory on Toronto’s Lakeshore Boulevard.
After several years, Mr. Rosen bought back half of his own chain but Dylex provided a lot of logistics. The Harry Rosen chain expanded across Canada to include 23 stores from Vancouver to Quebec City, according to Larry. In 1987 they opened a multi-storey store on Bloor Street, in Yorkville, a long way from the small shop a few miles to the east where the young Harry Rosen got his start.
The Posluns family and Dylex got into some difficulty in the mid-1990s and the Rosens bought back the remaining 50 per cent that Dylex owned. It has been a family-owned business since then.
There are currently 20 Harry Rosen stores in seven big Canadian cities. And the company now does well over $300-million of a business year, 20 per cent of it online. The business has stuck to Mr. Rosen’s original philosophy of looking for interesting clothing for men to wear.
“My father had a sense of style and panache,” Larry said. “He loved quality and beautiful, well-crafted merchandise. He dressed with such a unique point of view. He went to Italy in the 1970s and discovered the Zegna organization and brought them back to Canada. He brought Armani and Polo to Canada; he loved fashion and style and quality. He was a student of the world and he was the first major retailer to bring all these important brands to Canada and North America.”
The elder Mr. Rosen ran in marathons, not the famous ones in Boston or New York, but smaller events in Canada and the United States Along with running, Mr. Rosen loved music, especially music from Eastern Europe. He bought a mandolin and took lessons, and while he was at it picked up a banjo.
When he was interested in a subject, he dove in. Mr. Rosen also read a lot of history, authors like Barbara Tuchman, as well as writers like Anthony Bevor on the two World wars. He joined a philosophy club that met at Carman’s Club steak house (later renamed Carmen’s Steak House) in Toronto.
“He was very proud that we were able to keep Harry Rosen as a family business into a third generation and thrilled that two of his grandsons are in the business and able to carry on his legacy,” Larry said.
Harry Rosen leaves his wife, Evelyn; brother, Lou; children, Larry, Andrea, Wayne and Racheal; nine grandchildren and six great-grandchildren.
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