First off, I just want to say that I do enjoy the increased variety of clothing in passengers that TSW3 has introduced. I don't think I've ever seen one passenger that looks exactly like another, and I love that increased immersion. With that being said, I think whatever randomizer is used to populate the different passenger clothing needs to be tweaked in the case of hats. One thing that is immersion breaking is seeing passengers in a business suit or dress, but wearing a lime green baseball cap, or in a trench coat with a backwards pink hat. Obviously I don't know how exactly the algorithm works, but I can imagine that it's a fairly easy process to set a rule that if a passenger has on something more formal on the rest of the body that hats either be turned off, or be set to something more appropriate for the attire. I know it's a minor issue in the grand scheme of things, but just thought I'd point that out on the off chance this could be tweaked.
