The clothes and shoes are very typical for a sailor or powerboater as found at any of the harbors in Chicago- there are multiple harbors in that area- Montrose, Belmont, Burnham, Monroe, Diversey. These are fairly pricey items- belt, shoes, pants, etc. and it is hard to believe that this guy was not ID'd on Day One? It sounds like "his boat" went down or he went overboard in Lake Michigan. The only other thing I can think of is someone "passing through" where a boat may be missing but his family may not have any idea where the boat was at the time it sank? Or he took a boat out from one of those harbors but he lives alone and no one has realized he is missing. The boats are just going into the harbors now so he may have went down last Fall based on the appearance.