For me, keeping the head/neck, hands and feet warm is most important in the cold. When those parts are warm, I’m warm.
As the temperature drops, the heavier clothing comes out, but typically (40 or below, but over 30) I wear a hoodie with a light windbreaker, toke, thin work gloves, and two pairs of socks in the appropriate shoes for the weather, and I’m good.
You will get used to it to a point, but you will always feel the cold.
Californian in DC.
The first winter is the worst. After that, it kind of confirms to the whole scale you’ve always had. You’ll feel cold, but about the same misery level you were on cold days in your hometown.
One of the hardest things to get through my head was that gloves, hats and scarves are necessary to go outside. In more temperate climes, they are cute fashion accessories. But when it’s actually cold, you really do need to have these things on you if you want to go outside. If you leave them in your apartment, you have to turn around and go back and get them, you can’t just solider on without them. That’s a big change.
Anyway, don’t be too hard on yourself. Those same sweatshirt warriors would be a sweaty, exhausted mess in what you’d consider mild summer weather. Everyone has their own weakness.