I don’t mind winter. If it’s winter, I’ll wear tights instead of pantyhose, and even wear it in male mode. I have some warm long sleeve tops, and if I need more, I’ll add a cardigan or a blazer. I have some longer skirts and dresses that I can wear in the colder months too.
Outdoors, when it gets cold, I have a red calf length woolen trench coat for dressy occasions, and an ankle length puffer coat with a hood for other occasions, including walking through my neighborhood. With either I also have gloves which feminize my hands. The ankle length coat is such that I can wear any length dress or skirt beneath because the coat covers me. You can’t tell what I’m wearing beneath, and I’m still warm in a skirt. If the ground is wet I’ll wear boots.
I’m not a fan of biting wind. I can put on a scarf over my face, but it’s not nearly as effective at keeping my cheeks warms. The cold also makes my nose run, but that’s a minor annoyance; I just have to remember to bring tissues. Otherwise, I enjoy the change of seasons into cold weather. I get to wear outfits I wouldn’t wear in the summer.