Queeg wears Hawaiian shirts (he has a great collection, including some "antiques").
Queeg wears shorts (double-pleated khaki type).
Queeg does NOT wear tennis shoes except to play tennis. He wears well-worn boat shoes. Why does he not wear tennis shoes? He has these HUGE feet <wink> and if he were to wear tennis shoes, it would be a case of, "Feet? Where you takin' that dude in the Hawaiian shirt?"
He probably DOES look like a dork, but he prefers to think of himself as the wealthy yachtsman searching the local saloons for the hired captain so he can get the boat out of the slip.