My favorite urban hiking shoes are these Merrills, their Boulder style. Not sure they make 'em anymore. I would not use them for bouldering but they might work for that. Good for clambering on ruins, cobblestones, dirt roads, and plain sidewalks. I like those Prana hiking pants too. Lightweight, lots of stretch, can put long underwear underneath if it's chilly, and truly water-resistant because I tested them.
This footwear selfie in Rome last week.
What do you like for long urban hiking with cobblestones, slippery places, dirt roads, etc?