I wear skirts or dresses all the time, only own 2 pairs of trousers and no jeans.
I wear opaque tights autumn through spring, mostly brown or aubergine, occasionally black. If I want to 'dress up' I will very occasionally make the effort to shave my legs and wear 10 denier but they go straight in the bin at the end of the night as washing always snags them.
I find the secret with tights is you have to try lots of different ones to get the ones that suit your shape. And paying less than £5 a pair usually works out as less value for money as well as tending to be less comfy. I find M&S no good at all for tights. Once you've found the right make, buy up EVERYTHING in your size.
Summer no tights and pretty sandals with heels.