So, again, what to wear with heels during the winter?

I think it depends upon what type of heels you're wearing and the occasion. Personally, I feel more put together when I wear nylons with pumps, sling-backs and sometimes even dressier flats. I wouldn't wear them with a strappy shoe style. I'm pretty pale, so I usually opt for a shade of suntan or sometimes even sheer black if I'm wearing a dressy black dress and pumps. Smooth bare legs are also acceptable. (You can wear nylon footies inside your shoes.) Tights are still popular to wear with boots, too, if your outfit is more casual. The main thing is that you need to feel comfortable and appropriate for the occasion. With those things will come confidence.

I live in Canada, so I'm all about the opaque tights for all but the dressiest occasions! They look great with boots or booties, and I've certainly seen them worn with pumps. Knit tights are a bit more casual, while smooth fabrics look dressier. Black is the most versatile choice, but I think coloured tights are coming back again?

I agree with Wonderer. We must be twins!

It all depends on the temperature. If it's not too cold I will go bare legged. If there is a cold wind or it's frosty I prefer opaque tights. If it's an evening out and a bit more dressy occasion I like my patterned tights (chevron, spot, houndstooth, diamond) that are more semi-sheer. I never exactly enjoy wearing hosiery but it does look good with a dress or skirt when the weather turns cold.