I'm a fan of shoes that meet in the middle of both looking good but also comfortable. Some of the sickest shows you see are actually quite uncomfortable to wear.. because they are more of a fashion accessory. Currently I've got a pair of red low converse, got them when I was in LA. Also have a newer pair of low top supra's because now that they are broken in they are quite comfortable.
I'm looking to buy something fresh but it's winter now and shoes get ruined quite fast
Another reason why I can't wait to move to LA, where it's nice 24/7 and there is no snow/winter to ruin your kicks.