My favourite-ever trainers for with skinnies or skirts are Superga, but their hi-top version is not very, um, hi. (To be fair, they do call them mid-tops..)
I've never found Converse very comfortable so am avoiding them but can't find anything sensibly-priced that looks fairly similar in tan or maybe grey leather. I'm not averse to buckles and I love the Ash Virgin/Kurt Geiger Lizzy but they're ridiculously expensive. Has anyone seen anything that might fit the bill?