When it comes to cost-per-wear, a good pair of shoes has to deliver the most value of any item in a man’s closet. We can wear the same pair multiple times a week. A good shoe can last a man years—decades even, if he takes good care of it and employs a cobbler to refurbish and resole now and again. But you've got to spend your money wisely on the pairs that will work for you. Where do you start? Zero in on the brands known for their quality and choose from them, even if that means buying less. You will probably not need ever kind of shoe on this list, but there's no doubt a few could serve you well for years to come.