In other cities, such as Chicago, the city flag seems to be far more ubiquitous. Here’s what Chicago’s looks like:

In the case of Toronto’s flag, the two white bands are meant to represent the architecture of Toronto City Hall. The maple leaf is the Council Chamber at the bottom. And there is some suggestion of a letter “T” for Toronto. Wikipedia says the “T” is supposed to be found in the blue space between and above the two towers of city hall, but I’ve always seen the two white bands as being the “T.”
In the case of Chicago’s flag, the blue bands represent the lake and river (I like that) and the four six-sided stars represent significant events in the history of the city (positioned between the two bodies of water to mimic its actual geography).
Roman Mars of 99% Invisible has a great podcast and TED talk on this topic. (The study of flags is known as vexillology.) In both instances, he outlines what he believes to be the 5 rules of great flag design. They are:
Keep it simple
Use meaningful symbolism
Use 2-3 basic colors
No lettering or seals
Be distinctive
Toronto’s flag generally conforms to these rules. But there’s something about the positioning of the maple leaf that makes the flag feel a bit arbitrary to me. I want to rationalize it.
In any event, I think it could be really interesting if all of us shared our city’s flag in the comment section below and made a comment about how ubiquitous it is within the urban landscape.
Roman makes the argument that a great flag gives people something to rally behind. And with cities only becoming more important on the global stage, there’s something to be said about having a well-designed flag today.
I wonder if there will be a correlation between good flag design and ubiquity. My guess: probably.
“Toronto is a city that has long struggled to make any sort of impression on the imagination.”
That is how Monocle correspondent Christopher Frey started his recent architectural feature on Toronto’s iconic City Hall. To watch the video click here. It’s about 5 minutes long.
As a born and raised Torontonian who loves this city, I absolutely hate that sort of introduction. But at the same time, it doesn’t surprise me. Growing up in this city, there were always the haters. However, I think it’s important to keep 2 things in mind.
Firstly, Toronto has gone through a dramatic transformation over the last decade or so. In fact, I recently had a friend say to me: “Brandon, 10 years ago you told me that Toronto was going to be a super cool global city. I didn’t believe you then. But you were right.” This is what I was getting at in my Guardian Cities piece when I talked about how people are becoming noticeably more passionate about this city. (I actually wrote about what my friend said but they edited that part out.)
Secondly, if you’ve ever read Seth Godin’s book All Marketers Are Liars, you might remember this line:
“We believe what we want to believe, and once we believe something, it becomes a self-fulfilling truth.” -Seth Godin
— Brandon G. Donnelly (@donnelly_b)
To illustrate what he means by this, Godin uses the example–among many others–of Riedel wine glasses. Riedel is a high end glassware company founded on the belief that every type of wine needs its own unique glass shape. And indeed, their customers believe that the right glass makes all the difference in terms of how their wine will taste. That’s why they buy them.
However, when you blindfold those same people, they are no longer able to tell the difference between a Riedel wine glass and some cheap alternative. The wine all of a sudden tastes the same. What that tells us is that when we believe something is supposed to be better, we actually experience it differently. You could say that we’re actually lying to ourself.
And I’ve thought about this same phenomenon when it comes to cities. When people visit a place like New York they’re supposed to like it. That’s what everybody tells them. New York is great. You’ll love it. But ultimately, that “supposed to” changes how people experience the city.
Which is why when Toronto gets introduced as being bland and banal I get upset. Not only because I disagree, but because I know it’s creating a “supposed to” in somebody’s mind. And that’s not the story we should be telling as a city.
Image: Wikipedia
In other cities, such as Chicago, the city flag seems to be far more ubiquitous. Here’s what Chicago’s looks like:

In the case of Toronto’s flag, the two white bands are meant to represent the architecture of Toronto City Hall. The maple leaf is the Council Chamber at the bottom. And there is some suggestion of a letter “T” for Toronto. Wikipedia says the “T” is supposed to be found in the blue space between and above the two towers of city hall, but I’ve always seen the two white bands as being the “T.”
In the case of Chicago’s flag, the blue bands represent the lake and river (I like that) and the four six-sided stars represent significant events in the history of the city (positioned between the two bodies of water to mimic its actual geography).
Roman Mars of 99% Invisible has a great podcast and TED talk on this topic. (The study of flags is known as vexillology.) In both instances, he outlines what he believes to be the 5 rules of great flag design. They are:
Keep it simple
Use meaningful symbolism
Use 2-3 basic colors
No lettering or seals
Be distinctive
Toronto’s flag generally conforms to these rules. But there’s something about the positioning of the maple leaf that makes the flag feel a bit arbitrary to me. I want to rationalize it.
In any event, I think it could be really interesting if all of us shared our city’s flag in the comment section below and made a comment about how ubiquitous it is within the urban landscape.
Roman makes the argument that a great flag gives people something to rally behind. And with cities only becoming more important on the global stage, there’s something to be said about having a well-designed flag today.
I wonder if there will be a correlation between good flag design and ubiquity. My guess: probably.
“Toronto is a city that has long struggled to make any sort of impression on the imagination.”
That is how Monocle correspondent Christopher Frey started his recent architectural feature on Toronto’s iconic City Hall. To watch the video click here. It’s about 5 minutes long.
As a born and raised Torontonian who loves this city, I absolutely hate that sort of introduction. But at the same time, it doesn’t surprise me. Growing up in this city, there were always the haters. However, I think it’s important to keep 2 things in mind.
Firstly, Toronto has gone through a dramatic transformation over the last decade or so. In fact, I recently had a friend say to me: “Brandon, 10 years ago you told me that Toronto was going to be a super cool global city. I didn’t believe you then. But you were right.” This is what I was getting at in my Guardian Cities piece when I talked about how people are becoming noticeably more passionate about this city. (I actually wrote about what my friend said but they edited that part out.)
Secondly, if you’ve ever read Seth Godin’s book All Marketers Are Liars, you might remember this line:
“We believe what we want to believe, and once we believe something, it becomes a self-fulfilling truth.” -Seth Godin
— Brandon G. Donnelly (@donnelly_b)
To illustrate what he means by this, Godin uses the example–among many others–of Riedel wine glasses. Riedel is a high end glassware company founded on the belief that every type of wine needs its own unique glass shape. And indeed, their customers believe that the right glass makes all the difference in terms of how their wine will taste. That’s why they buy them.
However, when you blindfold those same people, they are no longer able to tell the difference between a Riedel wine glass and some cheap alternative. The wine all of a sudden tastes the same. What that tells us is that when we believe something is supposed to be better, we actually experience it differently. You could say that we’re actually lying to ourself.
And I’ve thought about this same phenomenon when it comes to cities. When people visit a place like New York they’re supposed to like it. That’s what everybody tells them. New York is great. You’ll love it. But ultimately, that “supposed to” changes how people experience the city.
Which is why when Toronto gets introduced as being bland and banal I get upset. Not only because I disagree, but because I know it’s creating a “supposed to” in somebody’s mind. And that’s not the story we should be telling as a city.
Image: Wikipedia
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