During evaluations, we put a range of comfortable boots to the test, including chic leather options for warmer climates, warm hiking boots, and insulated styles for the chilliest locales. Waterproof leather: While a boot made from regular leather is super stylish (and may be fine for chilly fall days or on dry terrain), it’s not the most insulating or waterproof material. However, boots made with full-grain or top-grain leather have a water-resistant coating, like the Nylon: A heavy-duty nylon is one of the best materials to look for in a boot made for snowy or icy days.