The answer to this important question lies in what type of outdoor adventure you are taking on. For hikes, climbs, or outdoor jobs in cold conditions, insulated outdoor boots will keep your feet warm and comfortable. And as you would predict, waterproof outdoor boots are essential for any adventures or projects where water is in play. Finally, you will want to decide on how much ankle support you prefer before you start your boot shopping. A low-rise outdoor boot will keep you quick and nimble on your feet, while a high-rise outdoor boot will provide a higher degree of ankle support, which can be crucially helpful while hiking, hunting or climbing.