21 Things to do in Chicago in the Winter (And What to Wear!) coldest day on record in chicago what to wear See (Anna) Jane. Warmest Outfits for January in Chicago Something Different X BarbiGia This one is for everyone whos asked me what kind of coat they need for a Chicago winter., The answer is it depends because winter here can be 60 or it could be 20, so Im breaking it down for My go to look for a winter night out Staying stylish and warm in harsh winter weather in Chicago Opinion chicagostarmedia.com