I'm just as good at rolling my ankle in boots as I am in shoes (note I'm REALLY good at it - I've felt my ankle bone hit the ground in full high top boots before). That being said, I've switched to trail runners 90% of the time (unless snow or REALLY uneven off trail terrain) and actually tend to roll my ankle less now. Some of that is general strengthening, but also my Hoka One One trail runners have a very wide footbed outside of where my foot actually is - so I think that helps too. The comfort is absolutely worth it for me. | 
