Avoid making the same mistake as most people. You don't have to have the shoes just because you have them. These are some rules to remember when you're wearing the 5 best sailing boots. Boat shoes are three-season shoes. They are not recommended to be worn in winter. You don't have to ask. It's a very finicky rule. These simple style rules will ensure that you're the talk of the town in a pair of boat shoes. You can wear them again, provided you know how to do it.