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I worked in the same building as Harper's Bazaar in NYC, and none of those ladies wore boots or socks, even in snowstorms. All I can think is that their feet were numb from years of stilettos.
I do this all the time, but we have highs of 60's and full sun. After dark the temps drop 20 degrees in about 20 seconds and that's when I wear my socks and boots.
One of my best friends has such an issue with this! I am not known to "dress the weather" very well and I do this all the time. I really just walk from house to car, car to work so even in the cold weather (like yesterday's 5 degrees!) it's not really a big deal to me.
Today when temps were at freezing, I saw a neighbor outside in the snow with a child of about ten. The mom was bare foot! I can understand no socks but am baffled by barefoot walks in the snow.