With a midi skirt, I prefer boots that go a couple inches higher than the hem. Having a skirt that comes over the knees, then a bit of leg, an ankle, and a foot just looks too choppy to me. A boot that goes all the way up past the hem lets the skirt swoosh or flow, or whatever it does, down, and then the eyes just flow smoothly down the boot shank. (This is directly contradicted, of course, by Gnger’s fab outfit with white skirt, bare fair skin, and white ankle boots. That shouldn’t work, according to what I just said, but she looks great! Maybe it’s the low contrast on her entire lower body, and then the black/white contrast with her top).
With skirts above the knee, I’ve worn tall boots and short boots (like the pix in my red boots I posted tonight).
I’ve posted pix of myself in boots and skirts before, wish there was an easy way to grab those pix and put them here. But even Facebook hasn’t figured out how to do that yet.
One other consideration is decorations on the boots. The buckles on my black boots tore up the hem of a skirt before I got smart enough not to wear them together.