I’ve long been a bit of a flag enjoyer (thanks, Paradox), so this article by Ned Donovan has really stuck with me: “Good design is ruining American flags”. Using a rather vivid metaphor of banditry in rural India, the author laments the convergence of American municipal flags towards simple, technically sound designs that fail only at a flag’s most important task: to distinguish.
From the article:
The British did to highway robbery exactly what the refiners do to flags. They took something various and local and difficult, and made it simple enough to draw from memory. Twenty cities, one flag. Stand a man from Tulsa in front of the winning twenty and he could not find his own.
For national flags, I am a strong supporter of flags that are bold and simple enough to draw from memory. But the subnational flag space is significantly more crowded, and you need to do a lot more to stand out. If that means offending the sensibilities of the North American Vexillological Association, then so be it.
Let flags be ugly.
PS. I will admit the flag for Newton, Kansas is awesome, though.

