I walk in it all...rain, snow, sleet, wind, down pouring rain, heat - you name it. I only took the subway to work twice in 5 years (once when I hurt my ankle and once when I thought there would be a lot of snow, but there was none).
My office tends to get really hot in the winter from the blasting heat that I always have my window cracked a little. Wearing short sleeves in the winter is common (and sometimes long sleeves in the summer when the AC is on). But getting to work in a short sleeved shirt? Not easy. Last winter NYC was cold and windy. I would make bets with myself when I was walking how far I would get before I couldn't feel my toes/fingers/ears anymore. It didn't snow too much, but the cold wind is brutal for walks. So this year, I was going to be 'smarter' about my commute attire.
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Next area to tackle is the legs. I wear normal pants. A few of my pants are lined but most of them are not. I wear these same pants all times of the year. I wear either trouser socks or knee highs, so there isn't much additional foot protection either. Naturally my legs get cold because the only thing protecting them is some cotton or whatever it is pants are made out of. This past summer I knew leg warmers were coming back...so when I was at a flea market, I picked up a pair to try. They are thin but long - so I slide them up to my knees under my pants and wear them to work. You can barely see them, and it makes a huge difference. I need to buy a few more pairs!
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As for scarves? Well, I learned how to knit after my breakup. More on that another time...but I have a TON of homemade scarves. My favorite is a thicker wool woven big, and made really long, so it keeps me warm all over my neck.
My last favorite winter item is my LL Bean boots. When I moved to NJ I bought these for our winter house chores (shoveling, etc). I barely used them since I moved out so quickly and they remained in storage for 2 1/2 years. But when I re-found them, I fell in love all over. They took a while to break in - especially the 'tounge' part, which was rubbing my leg the wrong way. But once that corrected itself, they have been wonderful. I walk through anything in them - massive puddles, mounds of snow, you name it. They have good traction when its slippery too. The only downside to them is they are huge / heavy. But considering the benefits, I don't mind.
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