Cold, snowy and windy weather isn't much about outfits to take pictures of but more about keeping warm. And it's also pretty damn dark most of the day so one might as well forget about natural light in photos.
But anyway, my point here was actually the one that you can very well use your summer dresses even though it's cold (well, when quite cold, not real freezing like minus twenty cold though), as long as you just layer right (remember?). Not the most sheer ones of course, but a good ol' cotton dress will do, preferably lined, worn with a long slip underneath, a blouse, cardigan and enough of stockings and socks.
I've been wearing some of my Trashy Diva dresses with wool stockings lately. The cardigan is vintage; a present from Ina for my birthday. The hat is from Made By (the Finnish version of esty). Lace up boots are old Vagabond.