I've lived in Canada for a long time, and used to dressing for the winter, but when someone from California asked about going to Chicago in December for Midwest Furfest in a Telegram channel about fursuit photography, I struggle to name all the pieces of outfit required, while not veering way off topic.
To my surprise, Wikivoyage has a guide for exactly this: https://en.wikivoyage.org/wiki/Cold_weather
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Wikivoyage, hosted by the same not-for-profit that hosts Wikipedia, have travel guides require readers to put in some work, even for popular places; let alone those less frequented by anglophone travellers.
But it also has a great section on general travel topics that you'll not likely to find in paper travel guides. Beyond weather, there are guides about air travel, baggage, electricity, pizza... and also guides to major airports, and a phasebook for many languages too! https://en.wikivoyage.org/wiki/Travel_topics
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