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I’ve worn skirts in that kind of weather before, it’s fine with long socks and a warm jacket :)
Growing up in Minnesota, the end of fall/start of winter where it starts getting below 60F is where I start feeling chilled, and 40F is “omg I’m dying”
But
After about a month of that my body adjusts, last night I took a 15 minute walk out in the 33F “heatwave” wearing nothing more than a t-shirt, jeans, and shoes
By the end of winter anything higher than 20F doesn’t feel worth wearing anything heavier than a light jacket or hoodie if I’m just making short walks between buildings and vehicles
Still probably wouldn’t go out in shorts though
Some people are just super-resistant to low temperatures. One of my best friends sleep with a box fan on medium mid-winter (and when he lived somewhere with adjustable windows, his would be ajar).
Meanwhile, I get chilly at 65 and can wear a coat in hundred degree weather.