Are ankle lace-up ankle boots a mistake if you have short calves? These shoes have the right amount of support and flexibility and can accommodate my inserts.
I tried pairing a pair of high-waisted skinnies with knee-high boots, flats and these boots. They're more comfortable than either knee-highs or flats for walking intensive days, so there would be a strong incentive to wear them, but they do make short calves look even shorter. I like the slightly punk style, and if I could get over the stump factor, I could see myself wearing this with skirts. The question is, would my eye get used to it? I imagine this is what people who are accustomed to heels feel when they're forced to wear flats.