Some rain boots can be stiff and unforgiving. Boots that will be used for walking the dog or getting you to work need some special consideration. First, take a good look at the insole. It should be cushioned and offer enough support. A boot that has no insole probably won’t work. Ankle length, lace-up rain boots are a good option because they have better flexion at the ankle and won’t rub your calves. Ankle boots fit more like a shoe, so you won’t feel like you’re clomping around while you walk.