Did you know New York City has a flag? It does. And it is LAME. It has a seal in the middle of it. Said seal has two people on it. I am against the representation of people on flags. They belong on currency and stamps. Not flags. I feel strongly about this. It's also a vertical tri-color, which is boring and way too colonial for my taste. And it has writing on it. Flags should not have writing on them. Basically, it manages to be both busy and dull. Really, the only thing it has going for it is that it is not as horrifying as the New York State flag.
The best flags are abstract and yet make total sense (Think of the flags of Japan or Texas. Both of them make you kind of go, "Yeah, I can see it. Rising Sun. Lone Star State. Gotcha."). I propose a new flag for New York City. Simple, refined, accurate. I don't know what that would actually look like.