If I wear a skirt, it tends to be long and flowy, except for business suits ... and even one of my suits has a flowy skirt (although not as long as I'd like ... me in the pale grey at mom-in-law's wedding last September.

Care has one of those fluffy skirts - it looked absurd in a good way on her, so I bought it for her (Torrid, of course).

I dunno, I think the witches would tend to dismiss boots that had extra stuff (knee height, for example) regardless of how sturdy they were!