It was the combination of wearing the CT's and driving his weight outward (in that ultra-wide stance where he's telling you to turn your feet forward) that concerned me. I've never had a problem with my ankles, but I wear decent cross-trainers (New Balance 851's) while I lift.
I get where you're coming from, but personally, I don't think it's safe to WALK in Chuck Taylor's. You catch something on the inside of your instep, and BANG! There goes your ankle for a fortnight.
I can't believe you played basketball in lowtops, Fedorable. Consider yourself one of the lucky few who didn't need ankle surgery because of it. I sprained my ankle twice in mid-tops, and once in high-tops, and the time in high-tops I was barely out a week. One of the mid-top sprains was severe, and I was out 8 weeks (fortunately, none of these sprains took place until after my high school career ended...I had been injury free my entire playing lift up until that point). I don't like high-tops now, because they're too clunky, and I feel like the chances of turning my ankle in them is increased. Some friends of mine turned me onto Kicksology and Kicksguide and now I research my shoes before buying. The Air Max Finishers are outstanding for saving your ankles when you think a sprain is already inevitable and in the making.