>>2536498>Where are you situated geographically, out of curiosity?
Currently passing my holidays in Uruguay, but I live in Argentina. The climate is the same really.
I don't really know about what to wear with cold weather honestly, I normally either look awful when it's cold or I just "freeze" (it doesn't go under 10C really, so yeah, it's tolerable).
First, avoid baggy jeans/cargo pants (same for sports clothes outside of actually using them for sports), and, if it's too cold, use thighs under tight jeans (I seriously don't know what else you would wear in the cold) so your butt doesn't freeze. Second, start getting stuff like sweaters (most look "alright" but there are some really good looking ones) and long sleeved t-shirts with long necks (or get yourself a nice scarf). And forget completely about hoodies. They're comfy, sure, but they have absolutely no place outside of your house if your plan is to look good.
Also, don't fall for the "fat saves you from the cold" meme. Look for thicker (cotton) shirts instead. They're normally more expensive (in my experience at least) but they save your tits from the cold.
You could get a pair of tall leather boots and use them with a jean if you want classy footwear as well, but I doubt this is relevant since everyone dresses like shit in winter anyway, and the snow will most likely damage them.
All this said, the best way to dress properly and with what you like, is wasting your time looking and clothes (at stores, magazines, online, it doesn't really matter) and buying them (or at least cheaper ones that look similar).
And, if you're not wearing the jumper because you don't think it looks good on you, nee-chan, you'll have to improve your self-esteem first.