As much as I fiddle around with the right length for cropped pants, I really like them. There are a lot of things I think I understand. For example, I can see that with flat oxfords, leaving only a tiny sliver of skin showing at the ankle bone works really well (i.e. the hems are pretty much right on the ankle bone), whereas with shorter crops, "filling in" that space with an ankle strap or the shaft of a bootie works equally well. I can also see that the colour of the pants relative to the shoes, or relative to my bare legs, can matter.
I have a quick question, though. I made myself a few pairs of cropped "flares" (well, more like cropped straight legs). The narrower ones are very, very light blue, so low contrast with my white legs, and I find they work with lots of my shoes -- even with flats. But the wider, darker ones really do look best with low-vamp heels. And honestly, low-vamp heels often do a better job of leg-lengthening than anything else with most pairs of pants (skirts and dresses, too). Why do they never get mentioned these days? Are they just way out of fashion?