Wow - how did I miss this yesterday? Fun discussion I've skimmed over the comments so far, and a lot resonate with me.
The first thought I had was - here's an example of age appropriate dressing - and only the 'youthful' should attempt this look. . . I wouldnt' have thought this look could really work at all except for Jonesy's pics showing variations that DO work.
It's like original pic is a sort of volume on volume with the dress that looks too big (cuz all we can see is the skirt) and the sweatshirt that is purposefully oversized.
My easy fix is shorter skirt to show kneecaps or smaller sweatshirt.
However, if volume on volume is part of the goal, then Jonesy 2nd photo did it better - with it's longer, slouchier sweatshirt, and even longer more narrow skirt.