“Any man can lose his hat in a fairy wind.”   –   Irish saying

Sometimes it’s a little embarrassing, especially when they all fall out as you open the closet door.  Hats.  I can’t tell you how many are piled in a jumble on the top shelf of my back hall closet.  I guess you could say I have a little “hat problem.”  Some people have shoe problems, or hand-bag problems, but my problem (at least at present) seems to be sailing hats.  Oh, and sailing books.  Actually, anything related to sailing, come to think of it.

As with most things, it all started innocently enough.   I was simply trying to find the perfect little hat for my very specific sailing needs.  For a fair-skinned person, sun is the mortal enemy, and so a baseball cap, which many prefer, just wasn’t enough coverage for me.  I needed a brim that went all the way around, stiff enough to hold its shape even in a good breeze, and a chin strap so it didn’t blow off.  Oh, and the brim couldn’t be too wide, because then I couldn’t look up and see the jib telltales, or whether the spinnaker was flying properly.  And it had to fit all my hair under it.  In short, it had to be “just right.” And if it looked good, well, that was a bonus.  I was ok with letting go of any fashion ideas I might have had, as long as it met the exhaustive list of technical criteria outlined above.

In my shopping travels, ever on the lookout, I’d see a hat here or there, and think that it just might be “The One.”  And so, I’d buy it, bring it home, and put it in the test pile for the next time I went sailing.  Surprisingly, there weren’t many that survived my rigorous testing – in fact, only one perfect little hat seemed to meet all my simple needs.  One.  And what about that giant hat pile in my back hall closet?  It functions now (laudably) as the hat supply for visiting guests.  There are worse fates, I suppose.

A word of advice: you really don’t want to be doing the hat testing thing while racing.  I learned this the hard way (no surprise), where, at a most inopportune moment, I realized that I couldn’t see well enough, and that the brim was flapping up and down (rendering its shade factor quite useless), the chin strap didn’t feel right, and that it didn’t offer nearly enough sun coverage.  To say it was distracting would have been putting it mildly.  It psyched me out.  Ugh.  All I could think of was adjusting my hat — never mind the sails!

Considering that this was somewhat of a scientific endeavor (at least in my mind), it was surprising to me that  people weighed in mostly on “the look.”  In fact, someone jokingly remarked that they didn’t even have to look at my sail number to know it was me – all they needed to see was the ridiculous hat I always happened to be wearing.  I decided to be flattered.  Plus, I bet they were just trying to get me not to wear my lucky hat, which seemed to be working.  Yes, I realize that I may have looked less than glamorous, but I felt a certain amount of victory knowing that at least I wasn’t going to be as wrinkled as they were going to be.  Ha!  I was following my own fashion trend, eschewing the popular baseball cap for a more matronly (dare I say sensible?) look.

As I mentioned above, all that searching wasn’t for naught – I did actually find a hat that was THE ONE.  I adored that hat.  It was one of my most prized possessions.  I wore this hat faithfully for two seasons, and it was my go-to hat — maybe even my lucky hat (!) — I wore it for every race.  In fact, I last wore this hat in a two-day regatta at a Club way across on the other side of Buzzard’s Bay.  We had to sail all the way back home afterward, and luckily, since it was a long trip, it looked as though we’d have a nice, fast run/broad reach all the way back to our harbor.  What a sail it was!  There we were, in a freshening breeze, on a beautiful spinnaker run, way out in the middle of Buzzard’s Bay.  The only problem was that very soon there was a little too much wind, and so we decided to take the spinnaker down.  Quickly.  As we had decided upon this maneuver rather hastily, I completely forgot that I had left the chin strap to my hat untied.  Well.  As soon as I stood up, that beloved hat caught the wind under its brim, and sailed away, high into the breeze, and then plunged into the sea, forever lost in the Buzzard’s Bay swells.  It was gone.  I was devastated.  We could never have found it, even had we gone back and looked.

And so, even now, the hall closet hat pile continues to grow, year after year, as I continue the noble quest for that perfectly elusive, “just-right” hat.  I still haven’t found it.  I like to think that perhaps, later that summer, some nice lady found my dear old hat, washed up on her beach, and thinks, even now, how lucky she was to have found such a perfect little hat.

Moral of this story?  When you are lucky enough to find that perfect hat, always buy more than one!

Deborah Bennett Elfers
I was practically born on a boat, though on a working lobster boat rather than a sailboat. In my early days, I sailed quite a lot on a Sunfish, but not very elegantly, as in our little neighborhood “fleet,” the boat was primarily used as a weapon in a wildly popular game of “kill the other guy!” Who could have imagined way back then, that one day I’d become so passionate about all things sailing?
Deborah Bennett Elfers
Deborah Bennett Elfers

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