Yes, I tend to avoid pleated skirts because they just add a lot of mass on your bottom half, add in chunky boots and you're an anchored hump that shuffles about with too much noise that makes everyone look down even more. It does work to size them up and wear on your hips and then they have more of that effortless waft but they're no longer midi length then. I also like the handkerchief hem versions. If you're more straight up and down in the hips pleated skirts seem more of a natural fit, I feel, as the pleats don't do warping weird things outward.
Zara boots are on the narrow side when it comes to shafts and they're also a bit lower, so don't think they'd be wellie like you'd maybe have the opposite problem as they don't look to have a zip so may only just about fit or not at all.
I think the pleather skirt would look odd with knee high flat chunky boots.
Sara Danius' clothes look lovely, as colourful as she was, I hope it brings in a lot of money.