mdp22
FNG
While not the most robust shoes, the various Keen Vent series has served me well at work in New Mexico. I hate waterproof shoes and boots just don't like the clammy feeling all the time.
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I'd lean away from boots unless you're carrying a lot or expecting rough trails. I have a pair of Altra shoes that are good for my wide, flat feet.No, not in my opinion you're not. Wet feet are wet feet, doesn't matter if the wet comes from water on the outside or you sweat them wet from the inside, they're still wet.
If you're going to be primarily urban, any reason you wouldn't just get a set of good supportive walking/running shoes? They're usually built to keep you a lot cooler than any boots ever are. The comfort for all day on your feet is also hard to ignore if you're not somewhere they're going to get beat up and/or you're going to get weed-seeds in your socks.