I have quite a few dresses, but they’re all summery - midi, short sleeves, fairly thin. I can layer a roll-neck underneath, but they still look a bit rubbish with tights.
So please inspire me: what wintry dresses (long sleeve? Jersey? Knit dresses?) are you wearing with black tights and boots? I think they look better on me if they’re knee length or above, especially with tights, but I might be wrong.
I have plenty of black boots - long leather ones, chunky biker ones, patent ankle with a little heel, so I think it’s the dresses that are the problem.