The March 12 1937 edition of the Toronto Daily Star contained three separate ads for men’s Stetson hats, which were deliberately grouped together, of course.

The first ad was an ad by the Stetson hat people themselves:


John B. Stetson (1830-1907) was the inventor of the cowboy hat. He didn’t invent any of the hat styles shown here, but his hats were popular enough that they were often named after him.

The next two ads were for places you could buy Stetson hats. Here’s one:


The firm was actually called Calhoun’s Smile Hat Shops Ltd. It was not run by a man named Calhoun – the manager was one Thomas C. Hopkins – so I have no idea what the Calhoun’s Smile reference relates to. The 97 Yonge store was the first of the two stores to open for business, and started up sometime between 1922 and 1927.

By 1942, the 97 Yonge store had moved across the street to 94-96 Yonge. By 1947, the 96 Yonge store was the only one left. It lasted at least into the 1960s, as it appears in the 1967 city directory.

Here’s the other hat ad:


Unlike Calhoun and his smile, Jess Applegath was an actual person. However, the 1937 city directory also lists a company named L J Applegath & Son Limited, which also sold men’s hats and shoes, and had six Applegaths working for it at four locations in the city. I was curious: when did the split happen? Or were the Applegaths unrelated, which would be a monumental coincidence?

I went looking back through city directories, and found that there had been two separate Applegath hat firms going back to before the 20th century:

  • The 1895 city directory lists Llwellyn J. Applegath making hats at 213 Yonge, and Applegath & Harbottle making hats at 89 Yonge.
  • In 1890, the two Applegath branches finally connect up: Jesse (as he was then known), Llwellyn J. and Llwellyn J. Jr. were all living at the same home address. Jesse and Junior were working at Simpson’s, and Llwellyn Sr. was making hats at 253 Yonge.

I guess that Jess just wanted to strike out on his own.

Both Applegath firms remained in business through at least 1962, with Jess holding on to one store at 85 Yonge and L J & Son (run by various Applegaths over time) in two or three stores at various locations. (I have no idea whether this was the original Jess or not – he would have to be quite old by now, but I don’t see evidence of two men named Jess in the directory.) By the time of Canada’s centennial in 1967, though, there was nobody named Applegath making hats in Toronto.

The Vintage Toronto group on Facebook has a photograph of the Jess Applegath store window from 1931, and the Toronto Archives Twitter feed has a photo of the L J & Son branch at 155 Yonge from 1913.

2 replies on “Hats!”

The J in L.J. stood for John – indeed Jess went out on his own after working with his dad. I believe I have some advertising items that read “L.J. Applegath & Sons” with an S before Jess went out on his own. Apparently not an amicable split either according to sn old article I have – they were in direct competition. Everyone was very successful though until the hatless trend. Jess had a few stores in Montreal too – and was also directly involved in the early stages of professional baseball in Toronto.


Jess is my great grandfather. My father, myself and my son all have Applegath as a middle name. I’m always trying to find out more about the split. It can be confusing sometimes as to which Applegath hats is being talked about.


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