If you live in a snowy region, then winter boots are an inevitable purchase for growing feet each year. Your best bet is to find a pair that's lightweight and breathable if you don't want a daily argument about putting them on. Hot and heavy feet are no fun. If you live in a warmer climate, but have a boy that likes to explore the woods, a pair of hiking boots is a good investment. And, of course, in just about every climate, it's always good to have a pair of rain boots or some sort of weatherproof boot standing by.