I am working on formulating my rules *for old age dressing.* Hehe. I think there are maybe a couple of key goals and many ways to achieve them. I think you want to be solid, discreet, dignified, and forthcoming about your age. Frankly, I think the easiest way to do this is let your hair go grey. If your hair is grey (or white), you can wear just about anything. Punky hair helps too for "cuter" pieces.

For skirted leggings, I feel it would be important to wear them with solid shoes, shoes with solid soles... sneakers, boots, loafers. Ballet flats are too much flimsy on top of flimsy, I'm thinking.