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Even as we appear to have crested the hypebeast-powered tsunami that is sneaker culture, there’s still no denying the sheer power of footwear. It’s virtually impossible to name an article of clothing more important, be it as a telling cultural signifier or rugged instrument of functionality. It should come as no surprise, then, that this editor has spent weeks seriously and pragmatically considering the merits of a forsaken sartorial style: the boat shoe.
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Ivy style isn’t just for fallBoat Shoes: A Brief History
There’s no denying a certain reputation around the boat shoe. Originally invented in New Haven, Connecticut (figures) and adopted by the ivy leaguers shortly after, the nautical-leaning style maintains close connections to a certain lifestyle, one that typically involves owning a Cape Cod cottage and running the family law firm. Even the name — boat shoes — invokes some serious culture baggage, of JFK and OCBDs, or worse, pledge-commits stanced up in their University of Georgia half zips and fresh Dockers.
This is not to say that boat shoes are explicitly uncool. There’s a real charm to the prep uniform, and likewise, photos of Paul Newman, Harrison Ford and Vampire Weekend frontman Ezra Koenig prove that wearing the style doesn’t have to telegraph trust fund. Better yet, the base of the boat shoe — leather or suede upper, easy-on design, often accompanied by a lug sole — check all the boxes we’re looking for in a post-sneaker society.
A New Era of Boat Shoes
In recent years, though, the boat shoe has undergone something of an evolution akin to that of mall brands. Sperry, once a bastion of the boring boat shoe, is now collaborating with the likes of skate brand Pleasures and golf darlings Malbon. Italian labels have covnerted the style from dock to runway with premium suede iterations and new palettes. Even Drake’s, the new standard for modern menswear, tapped heritage cobblers Sebago for a tasty little boat shoe capsule.
Equally essential to the great boat shoe resurgence is the return of prep (no, not that kind, although we love Adam) in the sartorial ethos. It’s no coincidence that styling boat shoes feels a lot more feasible in an era where J.Crew is the new Noah and brands like Rowing Blazers fill brick-and-mortar retail. There’s a renewed sense of smart casual and a drive to wear clothes that don’t start with sweat, all of which to say, boat shoes might just have a chance.
The Verdict: Are Boat Shoes Cool Again?
After extensive consideration, the answer to the boat shoes conundrum is, like so many other sartorial decisions, a big old it depends. Some fresh-out-of-the-box Sperrys and a UA polo shirt aren’t going to win you any points in our book, but with some intention — and one of the fire pairs below — boat shoes aren’t just a comfort comprise, they’re a straight-up flex.
The Boat Shoes to Buy This Fall:
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