The umpteenth resurrection of the boat shoe, the posh footwear par excellence that refuses to go away

Marivent, Mallorca, 1986. The Spanish royal family poses for its annual summer press photo, this time with special guests: the Prince and Princess of Wales and their sons. The moment, like everything else that the passage of time has made impossible to recreate, is iconic: two dynasties in the midst of apparently happy times pose, carefree, oblivious to the ups and downs the future will bring. Of all the details that a curious viewer can find in the image —and there are many: the matching outfits worn by William and Harry, the pastel shades, the nearly identical hairstyles of Sofía and Diana— there is one that could go unnoticed, but that also defines an era. It’s found on the feet: the men in the photograph, including the teenages Prince Felipe, wear the same footwear. A pair of boat shoes.

That moment, between the mid-1980s and end of the 1990s, marked the peak popularity of a shoe that, since its conception, has been associated with a certain social class. Its name made this linkage to the rich apparent, although it was not necessary to own a boat to wear it. Before the revival of the espadrille, it was the choice of the upper class (and those who aspired to pertain to that echelon) when the heat called for more casual attire. It was worn by both commercial pop stars and politicians on vacation, never with socks, and its design spread to budget shoe stores in more affordable versions. But unlike other garments, like the polo shirt, that managed to make the journey from the elites to the streets, the boat shoe has never been able to fully shed its aura of poshness. All the same, every now and then we see an attempt at reclaiming it, whether through cameos in hip-hop fashion or its inclusion in recent collections by Miu Miu and The Row. It’s a story of an accessory that seems made to be loved or receive the utmost of contempt, with no possibility of middle ground.

A shoe inspired by a dog

The image of the boat shoe as a garment for people concerned about inheritance tax is certainly not unfounded. We owe the design to a well-to-do businessman, Paul A. Sperry. In the 1930s, Sperry, an avid yachtsman, noticed that his dog could navigate any surface without slipping. The key, he believed, lay in the grooves in the pads of his paws. So, Sperry devised shoes with a sole that mimicked their shape in order to more firmly grip the deck of a boat. The material he chose, oiled leather, was designed to repel water. Sperry gave his own surname to the brand, which still markets the model to this day.

Like other garments associated with elite sports, such as the polo shirt, preppy style adopted the boat shoe as its own. This aesthetic first took shape on the Yale and Princeton campuses, and began to spread as the image of the young and casual version of success. Sweatshirts, bomber jackers, chino pants and, of course, boat shoes became popularly known as the wardrobe associated with a thriving, optimistic and dynamic socioeconomic class. The image of the American dream.

From then on, the boat shoe has become part of the ideology of country clubs, marinas and nightclubs in which a sneaker is synonymous with excommunication. For similar reasons, among other kinds of crowds it’s been simultaneously linked to the idea of the most rancid and immobile snobbery. The pendulum of trends, which is guided by units of time independent of prejudice, has swung back to the boat shoe on several occasions, occasionally attempting to strip it of the smell of men’s cologne and cigar smoke. For example, at the end of the last decade, preppy style was reclaimed by both hip-hop culture (in 2009, Kanye West designed white boat shoes for Louis Vuitton) and indie bands like Vampire Weekend. And so, every now and again, the same headline reappears: Are boat shoes back in fashion? Well, are they?

Get your foot off the yacht

“Forgive me, but are we talking to each other on the poop deck of a majestic schooner? Is the salty brine stinging my weather-beaten face? No? Then why the fuck are you wearing deck shoes, man?” So was Greg Hirsch berated by Tom Wambsgans on account of his attire in the first season of Succession. Waystar Royco’s offices aren’t the only place where the footwear raises eyebrows, despite the fact that brands like Timberland, in collaboration with Supreme, and Sebago have brought it into the modern era. “For me, the boat shoe, like the polo shirt, is completely outside my reality right now. I have lingering trauma from having to wear a school uniform,” says creative director and stylist Alfredo Santamaría, known in the online world as Gothic Sport. “Fairly or unfairly, the garment has been so pigeonholed that it is very difficult for me to see it in another context, even if brands try to update it.” What he does concede is its ability to endure and adapt to the times. “It is clear that they work and, as with moccasins, they will always be around. It’s also a shoe that we don’t know if it’s all-formal or all-casual, and that makes it all-terrain.”

At the other extreme is stylist and all-terrain personality Josie. “The boat shoe (white, in my case) is an aesthetic grounding in the planet because with them, you step on the world and you always walk through it with a very comfortable shoe that at the same time has a lot of personality, with that visual impact on your feet that evokes fresh air and sea wherever you are,” he says. He rose above the prejudices of the time to wear them. “In my twenties nobody wore them, but I dared because I’ve never been scared of a shirt with initials, not even a Teba [an unstructured jacket popular in Spain that recalls English countryside aesthetic]; so I’m not scared of any connotation associated with any clothes. For me, clothes and accessories are plastic elements in one’s favor, and so I’ve worn those shoes to my favor for 20 years, because nothing finishes off a look better than a dusty white boat shoe. Its cracked leather and the mileage behind it make the shoe a relic full of moments and worn spots that tell of places, happenings along your walk through this life.”

Amid the haters and lovers, fashion designers continue to try and make the most of the nautical silhouette. Last year, a collaboration between Saint Laurent and Sebago did just that by daring to use animal print. Just a few months ago, Timberland and New York house Aimé Leon Doré, which specializes in blending hip hop and preppy fashion, accomplished it with a model that recovers its classic essence. And even more recently, Troye Sivan catwalked for Miu Miu in Paris in a pair of boat shoes. Reborn or not, hated or loved, the boat shoe refuses to disappear.

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