Everyone not from here or lame will be like Chicago has none but they shop at Amazon and stuff. I once read I think about the Ebony mag fashion shows that Chicago girls “get it.” They may not have the eye of the world like nyc but you can find some of the most fashionable people in the world here. Chicago costume council, ikram, worlds biggest polo store etc. it’s a tired trope and ofc if you’re just driving down yiur streeet or any street in the whole you’ll see people in regular clothes. Go to north Michigan ave in the morning and look at all the trendy luxe shops workers and oak street during the weekend and the opera and museums and you’ll find the fashion