My winter wear is:
Tights and boots with short skirt, could be tweed, wool, cord, doesn't have to be denim, plus jumper or t-shirt and cardie.
Same but with a fuller, knee-length skirt.
Tights and boots with a fitted print dress
Or a simple knee-length jumper dress - I think a good quality long-sleeved jumper dress, that fits well and isn't too short, is a great grown-up look, with tights, boots/shoes, a bit of jewellery.
Casual suit trousers (ie not part of a suit, but made of suit-type wool) with top and cardie, plus boots or trainers.
Or just jeans and jumper. I like the ankle/chelsea boot thing this year, they work well with slim/straight jeans. I previously only had knee boots which was a faff with jeans.
I find winter much easier than summer!