Sperry’s Top-Sider Battles a Flotilla of Imitators

The storied 'boat shoe' not just for boatmen anymore

As legend has it, Paul Sperry—Dartmouth man, World War I naval officer—was sailing his cutter Sirocco on a cold day in 1935 when he nearly slipped on the wet deck and killed himself.

Apart from his near-death experience, Sperry also noticed how his shipmate (a cocker spaniel named Prince) navigated the slippery teak without trouble. Later, examining his furry friend’s paws, Captain Sperry noticed the fine ridges in the pads of Prince’s feet and had an idea. Taking a flat-soled shoe and a pen knife, Sperry cut deep grooves in the rubber, which not only furnished him with fine traction on the deck but also, after a few subsequent style adjustments, produced a shoe destined for legend: the Top-Sider.

“Sperry is the original boat shoemaker,” noted Mark Sullivan, the editor of industry pub Footwear Insight. “They have authenticity, a legitimate heritage, and they’ve always fallen back on that.”

And, broadly speaking, it’s always worked—especially following the 1980 publication of Lisa Birnbach’s The Official Preppy Handbook, which anointed the Top-Sider as the official shoe of the bare-ankled, navy-blazer set.

Of course, as the ads here show, sometimes a good idea is just too good. As early as 1977, when this vertical ad appeared, Sperry was already dealing with imitators (“we’ve seen a lot of copies”) and urging us to buy the “real thing.” And while the preppy trend lagged a bit during the 1990s, today the style’s as popular as ever—which means, as Sullivan said, “it’s become a crowded market.” Sebago, Ralph Lauren, Timberland, Rockport, Coach, Naturalizer—all just a few of the brands that today make some variation of the “boat shoe.”

But for Sperry (which still has a comfortable grip on majority market share), there’s been a more subtle price to pay, and it’s visible in this 2014 ad. As copycats have flooded the market with hipster variations on the boat shoe (some of which, like John Varvatos’ linen version, defeat the purpose of even using them on the water), the Top-Sider is today more lifestyle accessory than yachtsman’s gear.

In the old days, Sullivan said, “they were selling boat shoes to boatmen. It was a performance, salt-water shoe,” complete with waterproof leather and a white sole that wouldn’t leave marks on the deck. “But now,” he said, “they’re about romance and lifestyle”—laceless boat shoes and plastic boat shoes and even open-toed boat shoes. “Now you’ve got kids in the boat, and the boat’s not even in the water.”

As the Baltimore Sun’s late fashion editor Vida Roberts observed a few years back, “the old crowd … scoff[s] at these deck shoes for sissies” and, bigoted term notwithstanding, she’s probably right.

For the purist, however, Sperry still sells the brown, two-eyed “A/O”—which, if you don’t belong to the yacht club, stands for “authentic original.”

@UpperEastRob robert.klara@adweek.com Robert Klara is a senior editor, brands at Adweek, where he specializes in covering the evolution and impact of brands.