↑ comment by stoat ·
2020-10-04T18:55:21.036Z · LW(p) · GW(p)
For what's actually ideal, I would suggest (if you find it interesting) reading about technical clothing for mountaineering and winter camping and adapting that to city fashion -- but if you want some helpful more affordable tips, what works for me is many layers.
For example, long sleeve undershirt and long underwear from Walmart. T-shirt over the undershirt, cheap sweatshirt hoodie over that. Thin pajama style pants over the long underwear. For me anyway, this can be completely comfortable under an outer layer of only jeans and just an autumn jacket up to maybe -15C or -20C.
Thin cotton gloves under big mitts or heavier gloves. Thin socks under heavy socks. For items where it's more difficult to layer, such as a toque or scarf (or socks if shoes limit the room), wool is pretty good and is affordable, thick, and sturdy at Army Surplus stores, at least here in Canada.
I would also suggest, don't neglect extremities or any body parts. For example, I remember once my thighs being very cold wearing only jeans (no long underwear), even though I had an extremely warm parka and was walking briskly.
I've found personally that even fairly thin pajama type pants, if you have say two layers under jeans, can keep you pretty comfortable even up to maybe -30C. Since you have in mind a meetup, I feel that even for example students on a budget, could get extremely adequate winter clothing this way at a Walmart in Canada that would enable them to stand outside inactively for 3-4 hours at up to -25C, say.