I'm drawn to this look, it's very 'me' and I am slim, have the right face/hair that would work with it, but even though I never consider anything too young, maybe it's the skirt pattern, i don't know, reminds me of the 90's (love!) but I am not sure how or where I'd wear that style. It's neither dressy nor practical.
I am late 40's 
Now, if I did recreate this kind of look, I wouldn't be justifying Cabbages and Roses prices, sadly. Anything excess I have is spoken for. So I would perhaps try ebay or vintage. I already have a similar jumper..
I don't like midi lengths but do suit mini's. But is this style a bit too odd? I feel stupid asking this as I don't believe in rules, but not sure it's worth the effort.
Have at it MN, insult or adore it, I'm open to ideas!