I've owned Chucks since I was ten, and I always go back to them. Use them how it suits you, they're a great everyday shoe, a trainer, a running shoe, a plimp, mono blacks will get you into all but the strictest of clubs. Battered up Chucks are just as fashionable as new, and they hold together well. I'll usually get five years out of them before I manage to destroy them, and that's with real abuse, work, festivals, motorbiking (I know I shouldn't, but I promise I won't come crying to you if I break my ankle).
The sizes are slightly on the small size, so if you're a big 8 but a small 9, order a 9. New ones take about a day to get comfortable, and that's really all the breaking in they need.