Thanks for the feedback - it's fascinating! Neither of these looks are fab to me, and the second skirt was just a "have to get out the door NOW!" option.
The shorter top for a midi always confounds me, but as I'm losing weight i'm finding I have a waist and that may help me find better tops.
MNsara, knee length is not part of the question here - I know they work for me( phew, one thing less to drive me crazy).
The first skirt is a pleated j. crew skirt I've had for a while and suddenly fits again. It's just a LOT of leg, and I am short! It is definitely too short for work, but I agree that sassing it up for casual weekend looks is a good idea.
Different boots might help too. I wish I had time to take a series of pictures to compare. In any case, today I'm wearing a knee length skirt with a tucked-in buttondown top and can't wait to see how that goes over!