Signs

 Tom the backroads traveller hosts this weekly meme.

September 2025 - Toronto ON

 This Tip Top Tailors ad is really two ghosts signs in one, although the fainter yellow sign is very difficult to discern.    The company, which is still operating today, was founded in 1909 by David Dunkelman, a Jewish immigrant from Poland. Dunkelman started his first store at 245 Yonge St., selling tailored suits for $14.  

I'm not sure if Tip Top ever occupied this building or just placed its ad there.

Tip Top Tailors founded in 1909, famous for its beautiful Art Deco - The Tip Top Tailors Building, now known as the 'Tip Top Lofts' is a former 1920s industrial building converted to condominium lofts in Toronto.

Past Meets Present post.

Past Meets Present

Past Meets Present #PastMeetsPresent

Various - Toronto ON

The Tip Top Tailors Building, now known as the 'Tip Top Lofts' is a former 1920s industrial building converted to condominium lofts. It is located on  Lake Shore Boulevard West just west of Bathurst Street, near the waterfront. It was the former headquarters of Tip Top Tailors Ltd., a Canadian menswear retailer.

Designed by Bishop and Miller architects using Art Deco decoration, 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.

Circa 1930

Click here for a great article about watching a ball game in that stadium. The street beside Tip Top is now named Stadium Road.

In spring 2002, Dylex sold the property to Context Development, which converted it into condominium lofts. The conversion was designed by architects Alliance of Toronto. The conversion included the addition of six stories on the roof. The neon 'Tip Top Tailors' rooftop sign was retained and given a slant.

We have several personal connections with this building. Tip Top were John's client when he worked in MasterCard so he visited this building when it was still offices in the early 1990s.

We also know someone who lives in the building and have been inside the condos.

I also have a friend who told me that one of her first jobs was working in this building probably back in the 1960s.

Tip Top Building in the background with a Joy Gas Station in front, ca. 1980