Thank you so much for your comments and suggestions. The consensus is shorter tops, lower vamp shoes/fitted boots, and tucking in a longer top. My wardrobe just doesn't contain skirt-friendly clothing:
No short tops other than a few tanks (brown, pink, black, red)
Only one pair of low vamp shoes since I can't walk fast in pumps or ballet flats
No cropped cardigans
Only one waist belt
Kiwichik: I agree the boots in #1 are the best out of the lot. #5 boots are no good but I liked the color. I tried the gray jacket below (1) but it's still a bit dressy/formal.
Jenava: The boots in #1 and #2 are as streamlined as it gets on my legs. #1 is pretty dressy too. #4 is a simple pump. Do none of those work? Is the top in #2 too long? I felt that one was the perfect length. I liked the yellow color too but tucking it in just makes my short waist look even shorter.
Manidipa: Oh, how the camera lies to us! The skirt is at least 2 inches below my knee, hitting the top part of my calf muscle. You're also being fooled by my 3 inch heels in #4. A belt is a good idea - I would consider trying one if I already had one in my arsenal. I don't own a white or chambray shirt but I did try several cardigans and they always looked frumpy because they were long and not cropped. Thank you for the compliment on my glasses - I forgot to blank out my face, which has since been fixed.
Diana: Showing leg (or at least the shape) seems to be key to making a midi work. I will definitely be trying the belting trick while I accquire shorter tops, if not with this top, with a different one.
Fern: Hmm, the yellow blouse would work well with the boots from #2. This isn't a keep/return but more a "here's what I tried - any suggestions?" thread. I'm in the middle of a purchasing spree where I ask for feedback on a bunch of stuff, then decide what to keep based on love/need/budget. Part of my decision making process is to pit items against each other and if I could only fit one into the budget, the Jcrew blouse would win easily. I did love the blouse and intend to repurchase it as soon as it goes on sale.
I'm confident I could make this skirt work if I added a few more clothes to the wardrobe and experimented with belts, tucking, etc. Unfortunately, the skirt is also a little too small (see 2 below), I have 1 more week to return it, and I didn't lose my extra couple of pounds in the past 3 weeks. I need to wear a longer top to cover the creases, but this conflicts with the advice to wear a shorter top. I do have a few other skirts in the queue, so maybe one of those will make it into the wardrobe.
Thanks again!
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