I find it rare to see a well-dressed man in a hat. Supposedly that only exists on lamp posts according to a recent post of mine. Hats can be very becoming and add a touch of interest to one's look. Very much like how a scarf or tie adds interest to one's collar, a hat rounds out a look. The saying is, "from head to toe."
This black bowler is very much at home with a grey coat and brown attache.
As a hat enthusiast once related to me, "You have to wear the hat. Do not let the hat wear you."