Bro...u are overseas for so long.. used to the cold. We chao sng ppl in SG wear jeans for air con malls only. Outdoor how to jeans?! lol
Like I said earlier depends how long you gonna be outdoors for. And what the temp is. Any windchill? Damp cold or dry cold?
If you staying outdoors for long time even going to camp and sleep outdoors then yes should bundle up a lot
But if outdoors long time then is doing what?just stand around? Why? No fire to warm up?
If skiing will get hot even sweat one.
If just going out of building to car then drive to location then go inside indoors no need so elaborate clothing.
Get good gloves and head covering for ears. Hiking shoes can already.