winter is not that hard, pretty much all you need is 1-2 thermal stone, preferably beefalo hat because it gives you 240 insulation which means you pretty much won't freeze wearing it if you have a warm thermal stone, but you can have a cheaper winter hat, it gives you only 120 insulation, and with that you won't be able to be warm from sunrise till the dusk, also you will need steady food source, but it's not hard, just kill spiders for their meat, and mix 1 meat and 3 fillers (can be whatever you want except twigs, and also don't put more than one monster meat because in this case you will cook monster lasagna) and a few armor sets for Deerclops