I've used the same pair of lightweight waterproof Timberland boots for the last 10 years (in the Spring, Fall, and Winter). It's not a problem at all walking around a city (Boston & NYC) in them, or hiking outdoors. In the summer, I go with my barefoot shoes, but that's a luxury and not necessary.
I've effectively used hiking boots for city-life for years. Yes, they are heavier, and the first week you get tired of walking faster than everyone else, but then it becomes natural.
I'd love to have less stuff, but I don't know how that doesn't turn into simply having the wrong stuff.