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I'll submit a few with a slightly different angle: these buildings are still "there", but altered from their original design; in some cases almost beyond recognition.

Ontario Science Centre: R. Moriyama
Burnhamthorpe branch of Mississauga Public Library: also Moriyama.
The Eaton Centre: E. Ziedler
 
I might be in the minority, but I feel architecturally we are only recently really hitting our stride and developing what can be seen as a "house style". The loss of some of the classic Modernist buildings are to be regretted, but their counterparts are quite readily visible throughout North America. The Mies/Pei/Stone grouping and New City Hall aren't going anywhere and they are our true hallmark set pieces of Modernism.

The TD Centre wasn't innovative as far as Mies towers go, though, was it? More a summation of what he'd done before - a sort of "greatest hits" package with counterparts elsewhere. Pei was smart and subversive with his building, which appropriated the form and scale of the TD towers, twisted them 90 degrees, and changed the colour and texture. City Hall, yes, there isn't another Revell, or anything else from that era, that it could be mistaken for.

Howard's Chewett Building was a local, brick version of the Palladian palace-front style that Wood first used in England a century before with his design for Queen's Square, Bath, although the eccentric window-spacing didn't conform to the established model. Still, John Nash designed facades for Regent Street that had symmetrical but irregular spacing, so it wasn't a punishable crime. The brick Chewett Building also ties in with the Grange, Campbell House etc. as a local version of the established British colonial form. They're still ours though.

I agree with you about the evolving, current Toronto Style!
 
Pei was smart and subversive with his building, which appropriated the form and scale of the TD towers, twisted them 90 degrees, and changed the colour and texture.

It's interesting that earlier renders of CCW have it looking less like the TD buildings--with a slight outward pitch in the lower floors and the lobby filled with branching pillars that would have made the space resemble a geometric forest (the newest Unbuilt Toronto book has a good image of this).
 
I don't think that Cumberland & Storm's Mechanics Institute has been mentioned. Begun in 1854, located at the NE corner of Church an Adelaide, (and first home of the Toronto Public Library) it was an extremely elegant building, ultimately demolished in 1949:

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Interesting from a stylistic point-of-view, doyenne, is that though the exterior is clearly neo-classical, the interior is already showing the influence of those pesky Ruskinites with Romanesque-revival detailing:

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A view down Church Street, showing the Mechanics Institute on the left at Adelaide, and St. Andrew's across the street:

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Note the outhouses in the backyards of the row houses in the foreground and consider the health implications of a city full of such structures!

In response to an earlier post about St. Andrew's, I would guess the chief stylistic influence of a Scots Kirk would not be anything Sassenach (English) but the example of New Town, Edinburgh!
 
Another lost neoclassical church was the charming Richmond Street Methodist Church (south side of Richmond between Yonge and Bay), designed by William Storm, built in 1844, demolished in 1888:

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Bump.

1. Temple Building. Not much more needs to be said, especially when one looks at what replaced it. Would have been the perfect complement to Old City Hall right now.

2. General Post Office Building on Adelaide and Toronto streets. Grand post office building and a great terminating vista. Most expensive federal building in the country at the time. Especially bad considering what replaced it.

3. Provincial Lunatic Asylum. Already discussed in this thread.

4. Toronto University Armouries. Come on. Look at that and tell me University Avenue wouldn't look better with that building there. York County Court House is sterile and doesn't provide anything but coldness to the feel of the street. The Armouries on a grand avenue like University is just a perfect fit.

5. Original Union Station. Beautiful old train station, especially including the later Front Street addition. I think it would have done wonders for Front Street and the city if they kept it and were able to convert it into the convention centre or at least a meeting hall (a la Ottawa), instead of what exists today.

6. Toronto Board of Trade Building. Obviously a beautiful building, and the perfect complement to the HHoF across Yonge, and the Gooderham Building behind it along Front.

7. Toronto Mechanics Institute. Adelaide and Church would have been great if this was still there. First home of the Toronto Public Library as well.

8. Old Toronto Star Building. I was debating whether or not to include this because it was replaced by something that has an even bigger impact on the city, First Canadian Place. However, my love of Art Deco and it being what inspired Superman's Daily Planet makes me include it.

9. Old Bata Shoe Head Office. Not in a prominent location and not "beautiful and old", but it was a great example of a standalone modernist building that this city will regret ridding themselves of in the coming decades. At least it's being replaced by something (the Aga Khan Museum and Ismaili Centre), as opposed to a parking lot, cheap condo or nothing.

10. St. Lawrence District. This one's cheating a little, but imagine if this was all kept. I love Berczy Park, but keeping all these buildings would have given Toronto a truly beautiful and all-encompassing "old town" like Montreal and Boston.

There's a bunch I could have included but didn't have the space for it. Toronto has been really terrible with preserving its history.
 
Great list. The recent Bata demolition really pisses me off. The city should have forced the Aga Khan to be built around the existing structure. There was more than enough room to do so.
 
2. General Post Office Building on Adelaide and Toronto streets. Grand post office building and a great terminating vista. Most expensive federal building in the country at the time. Especially bad considering what replaced it.

Losing this ornate building (and the vista) for the concrete and glass box that sits there now is up on my list. Really how many of these nice street terminating vistas do we have in the city? Old City Hall? St. Mary's?
 
8. Old Toronto Star Building. I was debating whether or not to include this because it was replaced by something that has an even bigger impact on the city, First Canadian Place. However, my love of Art Deco and it being what inspired Superman's Daily Planet makes me include it.

Though remember that "bigger" doesn't necessarily equate to "better"; and that FCP was the least-critically-well-received of the complexes of its day--so it isn't quite a Mies-replacing-Carrere/Hastings situation here...
 
Losing this ornate building (and the vista) for the concrete and glass box that sits there now is up on my list. Really how many of these nice street terminating vistas do we have in the city? Old City Hall? St. Mary's?

University, Avenue Road, Spadina, York, John, Bay, Kings College Circle, Frederick, Wellesley, Adelaide, Front (looking west to Church)......
 
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^ Yeah, Toronto actually isn't bad when it comes to terminating vistas. That one is a shame to have lost though.
 
There are also a number of charming neighbourhood terminating vistas, like at Cecil and Henry Streets. One example of a vista lost and then found is that of the Church of the Holy Trinity, which lost its axial view from Yonge after the construction of the Eaton Centre, but then gained it from Bay:

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Eaton Factories behind Trinity Square, from {a href="http://archive.org/details/goldenjubilee18600teatuoft"}Golden Jubilee, 1869-1919{/a} (T. Eaton Co. Limited, 1919).

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