Interesting take on the skirt frill, pippop1 - I have a few flippy / frill edged skirts from a couple of years ago that I find I just can't wear these days. I thought I had just got bored of them / I had moved to a more minimal style, but maybe they do just feel a bit young for me now (43).
Also on older women, I think flippy skirts can potentially look dated & aging rather than fresh - a bit "Twiggy at M&S". (I say 'can' because it's very personal & there will always be people of any age who can style it to suit them).
OTOH I think shorts as day wear (tweed & opaque wool tights) is perfectly acceptable, so what would I know .
Shorts as evening wear is beyond me though, unless you mean pyjamas.
I do find it difficult to know what to wear at my age 51 (and shape - size 14 and five foot nothing). I liked a jumper I saw yesterday in M & S with the face of a panda on it, But thought it bit soppy for my age. I'm seeming to go for with plainer clothes but with wacky jewellery and bright scarves. Distracts the eye from the other lumpier middle-aged bits (she said hopefully.....).
I don't want to be one of those people who look young from the back and when they turn around they are much, much older than you thought they were because their clothes are too young for them.