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 ar

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.