I've been paddling and portagin in the northwoods for a couple decades now, and I still haven't figured out what the perfect shoe(s) to pack are. Here are some thoughts. I'm curious what other people think.
Muck boots, Chota, etc. keep your feet dry and happy, and are especially nice when the portage trail is foot deep moose muck, but they're hot, and if you step in water over the top you're screwed!
Chacos, Tevas, etc. are great because you can splash in and out of the water all day, and you don't have to worry about how deep it is, but if you are out of the boat portaging a lot, the straps rub your feet raw, and getting a rock stuck under your arch with a boat on your shoulders, a pack on your back, and 100 rods to go would probably qualify as cruel and unusual punishment. Also, stubbing your toe is a real risk.
Keens and similar are nice since they have a closed toe, but they are also prone to getting rocks stuck in them (though not as bad as Chacos). Being dedicated water shoes, they also don't tear tear your feet up as bad when you're hiking in them wet all day. I think the Newport H2s are my favorite, but I think I could do better.
Anybody ever try a pair of wading boots with just neoprene socks instead of waders?