Thanks for your opinion, Joyce. Unfortunately, I won't be able to wear the skirt with a gap, because the skirt comes about an inch below my knee, and the boots are about the same height. I checked it in the mirror, and there isn't a gap except when I walk (then you can see above the boot shaft a little bit). Actually, a gap can make me look stumpy (breaks up my leg line too much, and I'm short already), so that's probably a good thing. Also, I was glad there wasn't a gap because I will be layering leggings under the skirt when it gets cold, and I don't want them to be visible.
I would also be wearing the skirt with snow boots. How is that for fashion forward?