I'm loving dresses this winter, which I haven't done since I was about 20. I only have a couple of dresses so far, but on the lookout for more. I wear the dresses with booties, so I am still as comfortable as if I were in pants.
To make them work in winter, I choose dark-colored tights and matching booties. I also sometimes pop a cardigan over, belted on top of the cardigan looks neat. And I also like a pullover sweater on top, so the dress looks like a skirt at that point. Have fun experimenting and see what you like!