The perfect sailing hat

I HAVE BEEN SEARCHING for the perfect sailing hat for years. Still haven’t found it, but I’ve come close.

I lost my hat the very first time I sailed in a keelboat. I was just a kid, a cabin boy, standing up in the forward hatch of a beautiful Knut Reimers wooden racing sloop called Viking, owned by Fred Smithers, a lawyer who lived in Cape Town. We were crashing into a black southeaster near Cape Point when the afterguard decided to tack. The jib swept over the deck, brushed against my head, and wiped my hat off. I saw it floating away to leeward and knew instinctively that no-one was going to offer to go back for it.

Since then, I’ve tried many different hats, from knitted black watch caps to a bright red fisherman’s sou’wester, but none of them has fully met my requirements, namely the need to be lightweight, waterproof, windproof, and irresistibly attractive to ladies.

I notice that some famous cruisers such as Larry Pardey let themselves be photographed in wide, shady, straw hats that look pleasantly goofy but I know for a fact they can’t wear them when they go up forward to douse the jib in anything over 10 knots of wind.

I rather like the look of some European yachting hats, the kind you see them wearing at Cowes Week or when the Queen comes to inspect the fleet or say howdy to the members of the Royal Yachting Association or whatever. And those Greek skipper’s caps, which look so very dashing, have undoubtedly helped lure many an innocent maiden into the nether regions of floating gin palaces; but the trouble with all of them is that they won’t stay put in any decent wind. Besides, you need a lot more chutzpah than I’ve got to wear a cap adorned with captain’s gold braid when you’re only the skipper of a 26-year-old, 27-foot sloop like mine. The hat should fit the vessel as well as the man.

And it should fit the weather, of course. For example, around here last week it was blowing 60 and gusting 80 miles an hour. Just a few miles up State Route 20, in the Cascades, they were expecting 20 inches of snow overnight. And down here on the coastal plain of Puget Sound, it was all solid rain and inside-out umbrellas.

We hear a lot about hurricanes on the East Coast but they don’t even know we have hurricane-force winds on the coast here every winter, regular as clockwork. We don’t whine about it. We just tie our hat strings tighter around our chins.

Anyway, to cut it short, I eventually found that the most practical headgear for my part of the world was a good old baseball cap underneath a hood attached to an anorak or a foul-weather jacket. The hood should have strings under the chin, of course, so you can adjust its tightness and prevent the baseball cap from escaping.

Now you have a waterproof, windproof hat with a peak that keeps the spray off your glasses and the sun out of your eyes; a hat that won’t get knocked off when you lurch against the shrouds; a hat that can’t be brushed off by the jib when some fool decides to tack without warning.

It’s almost ideal. It certainly fits the vessel. The only problem is that it conveys a sort of rumpled homeless appearance, which seems not to appeal to nice ladies, even without the plastic bags around my feet. My aim for next season is to improve the look of this arrangement so as to convey more of a feeling of dashing nautical nerdiness. Any suggestions would be welcomed.

Today’s Thought
Ignorant people in preppy clothes are more dangerous to America than oil embargoes.
— V. S. Naipaul

Tailpiece
“My husband is so careless about his appearance. He just can’t seem to keep buttons on his clothes.”
“Maybe the buttons weren’t sewn on properly in the first place.”
“Oh, you may have a point there. He’s terribly careless with his sewing, too.”