Ah, the boat shoe. The once proud footwear icon has been, in many circles, turned humble in the last ten years or so. But as always, times-they-be-a-changin’ within fashion spaces.
You may have heard whispers. Hushed rumors that herald a mighty return. Could it be? Could the boat shoe be back in style?
Well, the truth is, they never really went out of style. Not truly. If anything, their rich history and newfound versatility is being recognized once more, and that means – they very well might be here to stay for good this time.
But What Are Boat Shoes?
Boat shoes, also known as deck shoes or top-siders, are an American classic invented by Paul A. Sperry of New Haven, Connecticut in 1935 as a utilitarian shoe to maintain one’s footing in slippery conditions.
They are usually crafted from leather, canvas, or sometimes suede. Typically, they feature a moccasin toe shape, as well.
A distinctive siping pattern is cut into their trademark rubber soles, somewhat resembling the grooves along a rubber tire.
This provides them with a no-slip, non-marking grip that is considered ideal for boating and deck activities.
The Cultural and Contextual History of Boat Shoes
The very name, “boat shoes” is indicative of their strong association with boat ownership, symbolizing a degree of wealth and/or status.
Despite being a utilitarian shoe in nature, used by fishermen and yachters alike, they have gained something of a preppy, ivy-inspired reputation in recent decades.
One only needs to briefly parse through a 1980s J.Crew catalogue to see the evidence in spades. In preppy circles, their inherent ruggedness took on a new meaning, and became heavily associated with either crisp white or brightly-colored deck shorts, polo shirts, and a good dose of “do you know who my father is?” attitude.
Not only were boat shoes popular amongst this crowd – they seemed to influence other shopping trends and anchored an entire uniform that defined generations.
Clothing brands like Vineyard Vines, Ralph Lauren, J.Crew, and others commanded looks that became briefly inseparable from the boat shoe’s implied aesthetics.
Only, for some reason or another, this look wasn’t always received well, appearing a bit tryhard to some and earning a bit of mockery here and there.
Perhaps their later life in fraternities across the country is what initially seemed to kill the boat shoe for a good chunk of the American public. While stereotypical “frat-bros” would not hesitate to view and describe themselves as “cool,” the rest of society, it seems, would disagree.
The aforementioned outfit consisting of colorful chino shorts, popped-collar polos, and boat shoes (often the iconic Sperry brand) became the subject of much meme-ry in the 2010s. And for a while there, it seemed the boat shoe was effectively dead.
Rarely seen except on the sunny beaches of Fort Lauderdale during spring break, worn by white-claw clutching college students who, on some level, have to be purposely leaning into the whole frat-bro look.
The Return of the Boat Shoe
But as always, the tides have shifted. Boat shoes are on the rebound, particularly in fashion-forward spaces. Which means a few brave pioneers are just now rediscovering them, and now you have the opportunity to do so, too. That is, before they truly re-enter the mainstream.
Heck, trends move so fast these days that by the time this article is published, we may very well be there already as a society.
The thing is, the rules have changed. Or rather, a whole new set of cultural associations mean that this time, we’re gonna do the boat shoe a bit differently. That means what we pair ‘em with. Where we wear them altogether.
Unless you’re specifically looking to replicate the frat-bro-of-old aesthetic, listen up! Here’s the game plan, gents.
How To Style Boat Shoes Today
First off, make sure you have a pair you love. We’ll recommend some brands at the end of this article, but make sure your boat shoes fit, don’t slip, and look fresh!
There are numerous ways to style boat shoes, but we’ll start off by reimagining the preppy summer uniform we were ragging on earlier.
Preppy Summer Redux
One of the things that often made the chino shorts of the late 2000s and early 2010s a bit lame is that often, they were cut far too slim and flat to demand presence.
While slim shorts can work in some contexts, boat shoes can benefit from a pair of shorts that have a somewhat wider thigh opening.
Bonus points for pleated shorts! They embody a charmingly dorky vibe to some for sure, but pleats will give them a bit more shaping and dynamism.
You don’t want to look like you’re being squeezed by your shorts. Let your legs (and other assets) breathe!
So what if you end up looking like a camp counselor from the 80s in the process? If we’re going to redefine the preppy aesthetic, we want to take it back towards its roots instead of catapulting it into twenty-first century trends where it doesn’t belong. That means going back in time a little and revisiting what’s worked in the past.
The length of your shorts is entirely up to your preference. Shorter lengths such as the ever-popular 5-inch inseam are a good bet, and even carry some historical reference! See just about any photograph of young JFK in summer attire if you want proof. It works!
A good rule of thumb is to just make sure your shorts end somewhere above the knee. Though even then, some fashion-forward folks today champion the longer short. It’s up to you, really.
While a plain polo shirt is a suitable top (avoid the popped collar, please), you can do a lot better, if you ask us. Consider a knit polo for something with a bit more texture, or a camp collar shirt. These can be worn regularly or even open over a ribbed tank that’s tucked elegantly into your shorts.
Traditionally, you’ll want to go sockless while wearing boat shoes. Just trust us on this one.
Boat Shoes and Business Casual
You might be surprised to see the two in the same sentence, but the fact is, boat shoes can be dressed up a bit for a somewhat elegant sartorial look in the warmer months!
The following recommendation is a somewhat involved and playful take on business casual, but we have no doubts you can pull it off.
Try pairing your boat shoes with a pair of crisp white trousers, in either cotton, linen, or even seersucker. As always – bonus points for pleats, and a higher waist!
Then, add a horizontal striped tee, either in a white/blue, red/navy, or similar iteration. Tuck the tee neatly and tie it off with a leather braided belt that matches your shoes.
Finally, elevate the look with a navy blue blazer with gold-tone buttons. The final look is one that’s highly nautical in origin, but elegant and sophisticated enough for the office or a cocktail party.
Looking to go a bit more daring? Consider adding a bandana or neckerchief in a contracting fabric around your neck for an extra personal touch. For such a small piece, it sure can add a lot!
The Anchor of Smart Casual
Boat shoes work wonders in smart casual ensembles, and they should be treated as such!
One recommendation to consider as a mainstay style option is to pair them with jeans. Denim and boat shoes look pretty great together, and their moccasin construction can help you lean into both rugged or refined aesthetics.
Try pairing boat shoes with dark wash jeans, a white or light-blue linen shirt, and a tan linen blazer for a refined yet relaxed look that’s as timeless as it is effortless.
A bonus tip? Consider cuffing your jeans. Something about the contrasting denim tones gracing a classic pair of boat shoes just pops!
Alternatively, try just a simple white tee shirt for something a bit more down-to-earth. Your boat shoes will complement the look!
Best Boat Shoe Brands to Try
Finally, a few specific boat shoe recommendations. Whether you’re looking to re-embrace these American style classics, or simply trying them out for the first time, here are a number of brands worth noting.
Sperry Top-Sider
Named after the creator of the boat shoe, Sperry patented his trademark slip-sole in 1939. The rest, as they say, is history. You simply cannot discuss boat shoes without mentioning Sperry. So ubiquitous is the brand with the shoe type – it’s kind of like when people call all tissues “Kleenex.”
Their original boat shoe designs are competitively priced, well-made, and ever-lastingly stylish.
Sebago
Established in 1946 in Maine, Sebago has built a reputation for quality products at a fair price. They stock a wide variety of boat shoe models and have wonderfully inclusive sizing.
Down to the styling, their boat shoes are charmingly classic and traditional – and well worth your attention.
L.L. Bean
The legendary New England-based sportswear company should be no stranger to you already, but their boat shoe offerings are mighty underrated!
While they offer several classic moccasin type shoes, their Casco Bay Boat Mocs are some of the finest boat shoe options you can get for just under the $100 price point.
G.H. Bass
Perhaps best known for their loafers, G.H Bass offers a fine selection of moccasin-style shoes as well, including boat shoes. Their Hampton Boat Shoe is sleek and refined, making it easy to style up.
For something a bit different, their Ranger Super Lug Camp Moc shoe retains many of the distinctive features of a moccasin boat shoe – with an extra dose of presence (and a platform lug-sole)!
Ralph Lauren
Where classic American style goes, Ralph Lauren picks up the trail, dusts it off, and makes it ten times better.
Their Merton Leather Boat Shoe is particularly nice, with a classic white sole that fits right in with an elevated preppy aesthetic. There’s even a stunning colorblocked red/white/blue version that’s splendidly American, and ultra-sharp, too.
Paraboot
The French Shoemaker celebrated and revered by menswear and fashion enthusiasts worldwide offers an exceptionally high-quality boat shoe for the devoted fan.
Their Barth model is crafted from supple leather and features refined stitching. They’re pricey, but a worthy investment.