Regarding dresses in winter:
I used to wear them and prefer them until I moved the south lakes in cumbria.
I tried everything to maintain it - buying thermal under layers, socks over tights, everything, but I feel as if I was forcibly dragged out of them.
I mean, once I stood for 20 mins at Kendal train station in January, a bit wet, windy, but terribly cold, and I was wearing a dress with two pairs of wool tights, a merino undervest, solid boots, two pairs of gloves, hat and scarf around my face, and I was FREEZING.
Very, very uncomfortable. My ankle length pure wool coat did nothing. It was soaked and heavy within 5 minutes and the damp/cold just seeped in through the wool. Even when it's not training here the wetness prevails.
I even purchased a huge wax raincoat and wore thermals underneath with skirts, wool tights, etc. Nope. Wind and rain and even mild drizzle get in through every slight gap.
After persisting with this for a while, I gave in and bought a pair of thermal leggings, and a zip up thermal jacket to put over my underlayer. More importantly I bought a Rab puffer coat. The cuffs and zipper and pockets are sealed.
The difference was immediate and mind-blowing. The climate barely affected me at all.
Wool really doesn't not cut it as an outer layer in such climates. Perhaps it depends upon how long you are outdoors per day and whether you use a car. I don't, and I walk a lot. It really was impossible, and I spent a fair amount of cash trying to make it work.
I wear very few layers now, but the right construction/material determines everything in that kind of environment.
I miss my dresses so sooooo much, but can NOT see me trudging through the lake district in a wool coat ever again.
And puffers tend not to go with dresses, nor most waterproof stuff. If anyone could suggest a solution then great, but I can't even remember the last time I saw someone in a dress here that wasn't a summer tourist or running to their office job.