Tip Top Lofts – 637 Lake Shore Boulevard

History of the Tip Top Lofts

The Tip Top Lofts are the quintessential Toronto loft conversion, located in the former headquarters of the 1920s mens’ clothing chain, and later redeveloped into a 10-storey mid-rise loft by the waterfront.

The gorgeous old Tip Top Lofts building at Lake Shore and Bathurst

There’s almost 100 years of history in this amazing Art Deco building. Designated a heritage property, the original facade and front lobby (one of the most gorgeous Art Deco lobbies anywhere in the city) were renovated and restored, and six additional storeys were added to the building. The bright red neon sign still hovers outside, tilted a new jaunty angle.

Great shot of the back of the sign, taken from the roof, before the conversion process began

Designed by Bishop and Miller architects in a wonderful example of Art Deco style, the building was completed in 1929 and housed the manufacturing, warehousing, retail and office operations of Tip Top Tailors Ltd., a menswear clothing retailer founded in 1909 by Polish immigrant David Dunkelman. Tip Top Tailors eventually became a part of clothing conglomerate Dylex Limited.

The Tip Top building is almost complete in this photo, taken from Fort York in the late 1920s

In 1972, the building was designated as a heritage structure by the City of Toronto. In spring 2002, Dylex sold the property to Context Development, which converted it into lofts. The conversion was designed by architectsAlliance of Toronto, with help from the preservation architects ERA.

Tip Top Lofts during the conversion process, with the addition under construction, probably taken some time around 2005

The conversion to lofts was completed in 2006 and now the Tip Top Lofts feature 256 lofts ranging in size from 600 to 2,580 square feet with over 50 unique floor plans. The lofts themselves are also unique; two stories high on average, they are spacious and comfortable. Most of the multi-storey modern designs are in the newer floors, while the original lower levels contain more standard lofts, single level with open concept plans.

Two storeys, high ceilings and huge windows in this Tip Top Lofts unit

Through all of the vintage lofts on the first 4 floors and newer units in the addition above, the north and east facing units have city views while the south and west units can see the lake from the higher floors. The spaces are more modern than most hard lofts, with a softer style than your traditional industrial lofts – lacking brick and beams (unfortunately) – and feeling more like a condo with high ceilings and concrete floors. There is some occasional brick in the lower levels, but the main loft feature is concrete.

Lower level vintage Tip Top Loft showing a bit of old brick beneath the warehouse window – a VERY rare find

The concrete floors and ceilings with giant mushroom columns between is reminiscent of the Wrigley Lofts in the east end, with the open factory spaces allowing for the large windows that were used to bathe factory floors in natural light. You can find a similar concept in the Merchandise Building as well, to some extent, though there is a lot of drywall hiding things there.

Massive warehouse windows sandwiched between concrete floors and ceilings are hallmarks of the Tip Top Lofts

Standing on reclaimed land from Lake Ontario, the existing building is founded on wooden piles driven down through the sediment and refuse to the bedrock below. These piles are all below groundwater level and, believe it or not, were still in good condition. In order to take the increased loads from the new levels, existing pilings were strengthened and new ones added. It was a rather arduous process from what I recall.

New piles being installed to stabilize the Tip Top Lofts building

The shore of Lake Ontario was originally the site of much of the nascent city’s industry. From wharves and docks came factories, then rail lines then roads and now residential. The lighthouse to the north of Tip Top Lofts used to be on the water front, for instance.

The old Molson Brewery (1955-2006) during renovations in 1969 (now the site of West Harbour City condos) with the little lighthouse, marooned 100s of feet from the shore – and the Tip Top building behind

From the Humber River to Bathurst Street, Lake Shore Boulevard is built on land infilled into the lake. The section east of the Humber was infilled in the 1910-1920s and was part of the Sunnyside Amusement Park development, which the road traveled through. The section south of Exhibition Place was infilled in the 1950s, at the same time as the Gardiner Expressway project (you can see the original shore line north of the Gardiner, where the land is elevated). The area east of the Exhibition was infilled earlier.

This aerial photo from the 1980s really shows how far the shoreline has moved. You can still see the vague outline of Maple Leaf Stadium almost 20 years later. BONUS POINTS – who else remembers Adventure Playground?

Lake Shore Boulevard was built partly through the building of new road east of the Humber River, partly through connecting existing roads. West of the Humber River, Lake Shore Boulevard West is the old Provincial Highway. East of the Humber was built in sections in conjunction with the development of the Sunnyside waterfront infill.

In the summer of 1930, workers are installing tracks on the Fleet Street extension

The old Lakeshore Road connected to Queen Street just west of today’s St. Joseph’s Health Centre. In the 1910s, an overpass over the waterfront rail lines was built to connect Queen Street to the Lakeshore Road at Roncesvalles Avenue. At the same time, Lake Shore Boulevard was built as a four-lane roadway east to the Exhibition Place area.

Streetcar and rail grinding car on the same piece of Fleet Street in 1961, 31 years after the photo above was taken

In the 1950s, as part of the Gardiner project, Lake Shore Boulevard adjacent to Sunnyside was doubled in width. East of Sunnyside, a six-lane road was constructed to the area of Bathurst and Fleet Streets. Lake Shore Boulevard in the downtown was built to connect Fleet and Harbour Streets and was a service road for the Gardiner. When the Gardiner was completed to the Don River, Lake Shore Boulevard was re-routed to Keating and the Keating Street section was renamed Lake Shore Boulevard.

Rear of the Tip Top building in 1978, with the Alexandra Yacht Club in the foreground

Tip Top Tailors was a Canadian menswear clothing retailer founded in Toronto in 1909 by Polish-Jewish immigrant David Dunkelman. He rented his first store at 245 Yonge Street and sold tailored suits for $14. The name of the chain was chosen by a customer in a contest. The now-landmark building that housed the manufacturing, warehousing, retail and office operations for Tip Top Tailors was built at 637 Lake Shore Boulevard West.

Detail of the amazing Art Deco styling of the Tip Top Lofts

This building was designed by architect and engineer Roy H. Bishop in in a classic Art Deco style, completed in 1929. Founder David Dunkelman’s son Benjamin Dunkelman served as president of Tip Top Tailors after his father stepped down in 1948 until he eventually sold the company to the newly formed Dylex Limited in 1967.

The gorgeous Art Deco lobby of the Tip Top Lofts, preserved the way it has looked since 1929

Note that it was Tip Top that caused the creation of Dylex, the company that bought them out. The two sides that came together to form the company had both tried to buy parts of Tip Top at different times. First there was the Posluns family, who for three generations had been involved in the Toronto garment industry. The Posluns were primarily interested in acquiring the company’s 5-story head office building on Lake Shore Boulevard. They had previously approached the Dunkelman family about buying the building alone, but the Dunkelman family declined the offer, wishing to sell the entire business if they sold it at all.

Tip Top Tailors lease agreement from 1962 – I thought they owned the land…?

The other party was Jimmy Kay, a Toronto-based entrepreneur with business interests in housewares, plastics, and lighting. Kay was more interested in buying the Tip Top Tailors chain of stores than the head office building, a proposition the Dunkelmans also rejected.

Great shot taken from Coronation Park sometime in the 1990s. Is there any photo that says “Toronto” as much as this one?

By 1967 Tip Top Tailors had lost its luster and had deteriorated into “an old broken-down chain” according to some. The Posluns and Kay had never met each other before (an auditor who worked for both Kay and the Posluns had arranged the meeting) but they were both interested in acquiring the same company, Tip Top Tailors. Separately, each side had failed in their bid to acquire Tip Top assets, but during the course of a lunch meeting they agreed to pool their efforts and offer the Dunkelmans the deal they wanted.

The rarely-seen back of the Tip Top building, sometime in the 1990s. Shots like this remind us that, as beautiful as it is, the building was a factory after all.

The Dunkelmans agreed to the joint bid by the Posluns and Kay, who formed a new company named Dylex (an acronym for “damn your lousy excuses”) to serve as the holding company for Tip Top Tailors. Kay and Wilfred Posluns, established a reputation for acquiring ailing retail chains and injecting them with new life, developing Dylex into a retail giant. Tip Top Tailors was the first example of a rapid turnaround – in its first year under Dylex control, the floundering 52-store chain regained its lost vitality, registering $37 million in sales by the end of 1967.

But gorgeous photos like this make us forget all about the industrial past

Still one of the leading specialty retailers in Canada, Dylex Limited continues to operate five retail chains that cater to distinct market segments. In 1999, the five chains comprised 640 stores, including 284 BiWay units, 113 Thrifty’s units, 109 Tip Top units, 74 Fairweather units, and 60 Braemar units. Additionally, Dylex operated two menswear manufacturing businesses, Weston Apparel and San Remo Knitting Mills, as a facet of its Tip Top business.

Inside the Tip Top Tailors building during the loft conversion process

One of the company’s signature traits throughout its history was an emphasis on maintaining sharply focused, niche-oriented stores that catered to a specific market segment. This characteristic endured into the late 1990s. BiWay operated as a neighborhood-based discount concept offering a narrow range of general merchandise, food, health-and-beauty aids, and family apparel. Braemar sold classically styled fashions targeted for career women over 35 years old.

The open industrial loft spaces of the Tip Top Lofts

Thrifty’s ranked as Canada’s leading jeanswear chain, selling moderately priced casual denim and denim-related clothing. Fairweather stocked fashion apparel for younger, contemporary working women. Tip Top, Dylex’s original chain, sold men’s clothing, suits, sportswear, and accessories. More than half of Dylex’s stores were located in Ontario, with the remainder scattered among the country’s other provinces.

Another before and after, showing the vacant building and the resultant lofts

Interestingly, Elliott Wahle was named president and chief executive officer in 1995. Wahle was a former director of player personnel for the Toronto Blue Jays (and had served as president of Toys ‘R’ Us Canada). The Tip Top Lofts building on Lake Shore Blvd. used to be right next to the old Maple Leaf Stadium, where baseball really started to take off in Toronto. Just an interesting “small world” type of thing.

Aerial photo from the 1930s showing the Tip Top building with Maple Leaf Stadium next door. You can also see the Crosse and Blackwell Building (now Rogers Media) east of the stadium and Loblaws directly north of that. The Toronto Malting Plant is at top right, in the same spot as today. And you can see the impact of the railways on the lake front in the early days if the city, there are tracks everywhere. SO much Toronto history this photo!

After a decline in its numerous retail enterprises, Dylex Limited sold the Tip Top Tailors chain to Grafton-Fraser Inc. in July 2000. Context bought the building 2002. Then May 2007 saw majority ownership of Grafton-Fraser sold to an affiliate of Gordon Brothers Group.

The view from the Tip Top Lofts’ windows now looks nothing like it did back in 1929

What’s really cool is that the Tip Top Lofts are connected to 2 other Toronto loft buildings. Over on Carlaw Avenue, in the east end, the Garment Factory Lofts were converted from an old clothing factory that was owned by Dylex. And across the road, the i-Zone Lofts was once a knitting mill, making raw materials that were used by that same garment factory. I love it when the little threads connecting old buildings emerge through the fabric of Toronto history.

But you can still see the remnants of the building’s industrial heritage

The Tip Top Lofts building is walking distance to Ontario Place, a quick ferry ride to Toronto Island and only minutes to the entertainment district or financial core.

The ugly old rear of the building has been cleaned up and turned into a lovely common area for all Tip Top Lofts residents to enjoy

As for neighbourhood, Harbourfront and the revitalized Queens Quay has officially reopened with new bike lanes, wider sidewalks and more green space. It’s a short trip to the Island Airport for a quick getaway and you’ll never have to worry about finding parking during the CNE!

Current Listings at the Tip Top Lofts

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