When it comes to waterproof boots, you need a pair that’s as reliable as a mailman: they should be able to handle rain, snow, and gloom of night—and still help you swiftly complete whatever it is that you’re trying to get done. With winter around the corner, now’s the perfect time to begin breaking in a new pair that will keep away the slush all winter long and still look great when April brings those rain showers. Below, our favorites.