I’m a lifelong, card-carrying rag sailor. But the sail I hoist isn’t the only reason the term fits. I know that, like wine, sailing clothes improve with age.
Take my two sailing shirts: both long-sleeved Lacostes, one navy blue, the other white. The backs of both have enough holes to rival cheesecloth. The cuffs are tearing away from the sleeves. The darker material of the blue one masks most of its stains, but the white one advertises them—slashes of green bottom paint, rust-colored blotches, speckles of varnish, a grease stain of unknown origin.
I’ve worn these shirts as long as we’ve owned our 12-foot catboat, Finn—almost two decades. They’ve become old mates of mine, and the rips and stains and frays testify to the many years of service they’ve seen aboard our yachtlet. Catch a whiff of them in their postsail state and, if you’re like me, you’ll relish their aroma of seawater, salt, sunscreen and sweat (and perhaps Pilsner Urquell).
Indeed, though they were once crisp shirts-about-town, the well-marinated state they’ve reached makes them boat-wear only. My wife, Ellen, sees to that.
She knows my penchant for wearing sailing clothes that are, if not technically rags, at least comfy to the point of scruffiness. Polos, chamois shirts, swimming trunks, hats, shoes…. How many times over the years have I tested her goodwill by wearing clothes that should have been donated to Goodwill?
This tendency to look like a seagoing hobo came early to me. By age 5, I was a connoisseur of rumpled khakis and baggy jeans. I still remember how pajama-like one pair of khakis had become. My mother ironed patches on the knees several times over, and I loved wearing them rolled up pirate-style, as I did with my jeans.
One of my favorite articles of sailing clothing when I was a sea pup aboard the boats we chartered and owned was a white sweater with a Swiss cross on its front. I wore it as much as possible, maybe because I equated it with my father’s Swiss Army knife that I coveted. I slept in it, burrowed away in a cramped forward berth. I probably even got my hair cut in it—the signature crew cut my father administered with clippers and buzzers. (Dad also used to summon me home to dinner by blowing on a conch shell Hawaiian-style, and I’d come running, likely in those same khakis—the knee patches muddied and grass-stained.)
I’ve never seen another sweater like it. I’m still looking for a similar one—an attempt to embrace my sailing roots, I suppose—even though long ago I lost the Swiss Army knife that my father bequeathed to me.
When I was a commercial fisherman, I lived in codfish-bloodied jeans, a hand-me-down blue-plaid flannel shirt, a pair of canvas sneakers bought at Kmart for $3, a royal-blue oil-splotched down vest with rusty snaps that I found at a thrift store and, on trips offshore, rubber deck boots and orange Grundéns oilskins—the true uniform of the trade. Those too bore blood flecks, scrapes and raggedy cuffs.
When my mom got gussied up before a night out, she said she was putting on her “glad rags.” I feel the same way when I put on my sailing shirts. I’m getting ready to party on the water with friends.
Clothes are mere objects, I realize, and yet they’re companions of a sort too—crewmates that have embraced me on sails spanning from the sublime to the scary.
Being a rag sailor binds me, as it does all of us who sail, to sailors from St. Brendan and Columbus to Cook and Melville. I wonder: Did they tooforge bonds with their attire?
Henry David Thoreau appreciated the importance of old clothes. In a journal entry from 1858, he writes: “Dec. 26. Call at a farmer’s this Sunday afternoon. I surprise the well-to-do-masters of the house lounging in very ragged clothes … I am glad to know … the actual life of these New England men, wearing rags indoors which would disgrace a beggar…”
I still mourn the tattered khaki baseball cap emblazoned with “Salty”—the name of our beloved yellow Lab—which got swept overboard during an unintentional jibe. No amount of searching could retrieve it.
And I believe that while sailing clothes might not improve in looks as they age—if you fancy the spiffy and the spotless—they do grow richer in character and comfort.
I will continue to trot out my shirts and my current battered sailing hat the way I did my last pair of Top-Siders. They were blue ones that turned powdery slate with countless rinses in salt water and developed such huge holes in their sides that the last three toes on both my feet waggled free.
One day, these two old friends, derelict at last, will disintegrate. Or someone in our household, namely first mate Ellen, will deem them too disreputable for wear even on the water, and I will consign them to the deep to mingle with the remains of my long-lost cap.
