A good pair of winter boots in Canada can last many years and get you through multiple winters. While typically, winter boots can last for at least five years, it really depends on how much wear you put on them. Those who only wear their winter boots for a few snowy occasions each year may be able to get close to ten years of wear out of them. Canadians who wear their winter boots on a near-daily basis during the colder seasons, though, may find they only last a couple of years.