Even when I was a teenager, it was a big thing to show that the cold didn't affect you (apparently).
My dad cleaned up schools for a living when I was in HS and they gave him dark blue pants, light blue short sleeved button down shirts, and dark blue jackets to wear. He was about to throw a jacket out one day because a dry cleaner messed up and dissolved all the insulation, just the outer shell and lining were left...I thought it would be cool to look like a working man and he let me have it. This thing made a hoodie look like a parka for an Antarctic expedition by comparison and it became my winter coat...it kept the wind off of me, but did little to protect me from cold, snow, rain, or anything else. Being as how we lived near Chicago, there were plenty of times I was cold in it...but I really didn't care, I liked the look and feeling like I could tell the elements that I was in charge. Very few kids that I knew would ever wear something like a heavy parka to school, it just made you into a target for scorn...
I was a little bigger than dad when I snagged the jacket but then had a growth spurt, so the thing was ridiculous on me by the next winter. I talked dad into buying me a surplus US Army field jacket (M65??) and then I had a great combo of something that was warm and that I also thought was super cool! I'm sure most of the kids in my HS thought I was some combo of a poser and a dork, but I didn't care...
Now, my top concerns for winter outerwear are warm and dry and I don't care much about the looks. Tried an Australian waxed cotton heavy jacket some years ago and didn't like the feel, then I gave up on leather because of the weight and not wanting to wear it in rain and snow. I just wear regular LL Bean/Columbia/North Face type stuff and don't worry about it being plain looking, plus I have a long wool JC Penney coat I bought for a song during the great recession for really cold days with no snow (like tomorrow).
Going to be cold here soon, but nothing like the Midwest is right now. I hope all my friends and family in my old stomping grounds stay warm and safe! I remember one bad stretch in our house in the NW suburbs of Chicago when it was painful to get within 10 feet of the door into our garage from the kitchen, much less even think about going outside....