So what, then, is a fellow to do? The answers vary. For many men, it's easy to simply take refuge in the fact that pyjamas now suffice as clothing practically everywhere these days and cover up in some high tech waterproof camping stuff. Or you could just stay inside.
Fortunately for me, I live in New England, near Boston, in the epicenter of that uniquely American style of dressing up with extreme elements of casual leisure thrown in, of combining proper dress with sensible dress in just the right way. Fortunately for the rest of you, this way of dressing not only happens to be enjoying a moment of fashion right now but is also far more generally acceptable in more places than ever.
The overall effect is a perfect fusion of correct and sensible, if a little laid back in its way. But that is the very heart of what this stuff is all about. Don't forget that above all the clothes should fit well, if even a little slouchy. Remember that when this "preppy fashion" moment passes and you should be able to wear this stuff for the rest of your life. Then your boy can wear this stuff for much of his life.
Oh, and your feet will stay dry.