It comes over as either somewhat old fashioned and paradoxically un-nautical, more at home at a fancy dress party, and with a whiff of camp about it as well.
Real sailors know that such hats would be blown away come the first gust and instead have eyes sunken into the skull to escape the salty spray (in theory anyway).
Now I have a boating trip coming up shortly (more anon) and was going to go hatless, until my brother-in-law made a very good point. When, he said, I let my nephews and nieces have a turn at the wheel what could be better - to make it official and show the importance of concentrating on our course - than lending them the skipper hat's.
Hmmmm..... this might require further consideration.....