When someone says “rain boots,” most people picture a rubber Wellington. Rubber is durable and flexible, and will stand up to mud, dirt and any other unwanted invaders. On the other hand, it won’t stretch, so it’s imperative to make sure your boots fit properly. Your toes should clear the top of the shoe comfortably when it’s on, and you should be able to lift your heel easily (but not too much). If you have to choose between sizing up and down, go up and wear an extra pair of socks, which will add comfort too.