I might have come along a little too late on this thread(I'm new here)..
but, I created/manage a website called
The MidWasteland. I started the site because of people like you( most of you) that think the mid west has no style.
The MidWasteland is DEDICATED to proving everyone wrong!
I think someone even posted a few of my street style pix. Those aren't even the half of them. Look through the entirety and you'll see.
And btw, sunday's best was the pooooorest attempt at capturing Chicago street style. It's unfortunate that people based their views on Chicago due to that blog.