I never liked shoes. As much as I value them for footing, protection, and all that obvious jazz, I find the toebox in general to be an offensively constricting contradiction to my very being. Shoes, to me, are pedestrian prisons.
And yet, having traipsed, trodden, tripped, and tumbled aboard enough boats and around enough marinas in my handful of decades to date, I really ought to know better.
I have suffered a compound fracture 20-something miles out to sea; I have taken innumerable urchin spins to the heels wading the flats; I’ve contracted Staph forging my way between tenders and dry land; I’ve had the tip of a toe sliced away (and stitched back on) while trudging through boatyard scrap metal, and so on. But pain is amnesiac, and, as they say, there’s no cure for stupid.
But then, just the other day, I watched my son stub a toenail clean off on a piece of dead coral at the beach. That, for reasons obvious to any parent, registered differently. My instinctive thought was to find him some shoes that might be a match for the craggy limestone beaches we frequent in the West Indies, which we now call home.
Looking down at my pathetic $3 shower flip-flops—I tend to leave them ashore when I surf and fish, and they often grow feet of their own—my mind wandered onto the subject of my love-hate relationship with my Sperry’s Top-Siders.
Love: Because they are a simplistic but rugged, rough-and-ready choice for most any activity. Hate: Mostly due to their (and my own) very undue connotation of unabashed preppydom. So we’re both from New England. What of it?
But ultimately, I think of the times we’ve had. We’ve sailed in regattas and dined at the yacht club, I’ll confess. But we have also skateboarded in raggedy jeans, we have summited mountains, we have fished and hunted, dressed bluefin tuna and whitetail deer. We’ve hitchhiked, dirt-biked, gotten lost in the jungles of southeast Asia, wet-waded trout streams in the Antipodes. We’ve been stained with motor oil and bottom paint, and shown up, with hardly so much as the wipe of a wet cloth, at a (very nautical) wedding only hours later.
The heavy-duty stitching, the full-grain leather, and Blake-stitched soles just seem to last and last. They’ve proven impervious to just about anything and everything my various lifestyles over the years have thrown at them. They’re also a pretty, tidy-looking shoe—if perhaps a little spartan. But that lends charm, and pairs with just about any outfit. They can be dressed up or down, and with a bit of the holy trinity of sun, salt, and H2O, they break in quite effortlessly, much like a good catcher’s mitt.
Form aside, the Top-Sider’s provenance is rooted in function: Founder Paul A. Sperry drummed up the design in Connecticut in the winter of 1939 while marveling at how his cocker spaniel, Prince, could frolic about in the snow and on the ice without slipping and sliding. By November of that following fall, he was filing a patent for the very shoe that I, and perhaps you, too, choose above all else nearly a century later.
So maybe it isn’t quite an effigy, my snot-nosed inner punk’s deliberate attempts to desecrate them with use and misuse. Maybe I’m actually wearing them for precisely the reasons they were made after all: Good, hard, unadulterated fun. Plain and simple.
I will continue my lifelong devotion to Mr. Sperry’s creation, with all due appreciation and respect. And if I have any say, so too will my son, his son, and his son’s son. And so on. Onward, from here to eternity, with Sperry’s Top-Siders.
This article originally appeared in the May 2026 issue of Power & Motoryacht magazine.
Info: sperry.com
