The May 26 1921 edition of the Toronto Daily Star contained a large number of ads for clothes and home furnishings. I noticed that many of them were concentrated in a five-block stretch of Yonge Street between King and Dundas.
I’ll do these in order from south to north. First up was Fairweathers, at 88-90 Yonge:

You can still see their sign on the Yonge Street storefront where Moores is now (this building is now listed as 100 Yonge).
Next up is G. Hawley Walker, at 126-128 Yonge:

Walker’s were gone from this location by 1926. Moving a little further up, we have W. & D. Dineen Co., Limited, who sold hats:

This store appeared in the 1926 city directory at this location but not in the 1931 directory (I checked at five-year intervals).
To get to our next stop, you have to hike to 211 Yonge Street at Shuter. (On the way, of course, you would have passed both Simpson’s and Eaton’s, both of which sold everything imaginable.) Here, you will find the Adams furniture store:

This store was at this location until at least 1951 (I didn’t check after that).
Just up the street from Adams was the John Catto Co., Limited, which sold dresses:

Catto’s appears in the 1931 directory, but not 1936. If you don’t find what you want there, you can cross the street to Northway’s at 240 Yonge:

I love the heading “summer joys call for immaculate white skirts”. This store proved also to be long-lasting – it appears in the 1951 city directory.
While the ladies were shopping at John Catto’s or John Northway’s, the men could toodle up the street to Fitzpatrick & O’Connell’s at 254 Yonge:

This store appears in the 1931 directory, but not 1936.
Or the gentlemen could go up to the English & Scotch Woollen Co., which was oddly nation-specific. This is not surprising, I guess, given that Canada was a British colony.

Clearly, Friday was the day to do your suit shopping, but not for long: the 1926 directory lists this location as simply “Vacant”.
After all this walking, you’re going to need some new boots. Fortunately (if you’re a man), the Walk-Over bootshop at 290 Yonge solved this problem:

Walk-Over proved to be long-lasting – they appear in the 1951 city directory.
If you were looking for furniture, and didn’t find it at Simpson’s, Eaton’s, or Adams, you could try the Dale Furniture Company at 304 1/2 to 308 Yonge:

Actually, the 1921 Toronto city directory lists the Dale company at 304 1/2 to 308 1/2. By 1926, they were at 304 1/2 to 310; this didn’t help them for long, as they were gone from this location by 1931.
Finally, there was the Brass men’s clothing store, which had four separate locations on Yonge (“Adelaide and Yonge” turns out to be 116 Yonge):

That’s saturation coverage! (The 97 Yonge store is actually new; it’s not in the 1921 city directory, so it must have been opened after the directory was printed.) By 1926, only the 116 Yonge and 148 Yonge locations were in business; by 1931, the 116 Yonge location was the only one left, and it too was gone by 1936. Perhaps it wasn’t that good an idea to be, ahem, as bold as brass. (Sorry.)