According to Esquire, there’s a boat shoe trend going on. Of course, they’re not your father’s boat shoes. That’s probably because not much that was once your father’s is your father’s anymore.
Though a staid classic of maritime casual wear, and a favorite among style icons like JFK and Paul Newman, they have, over the years, also developed an unfortunate association with the Tucker Carlson set.
Finance bro jokes aside, though the shoes do currently call to mind a certain strain of preppy frat culture, the fact is they’re much more of a blank canvas than most people realize—one on which people can project their own personal connections.
That’s the thing about boat shoes. Sure, JFK wore them. And yes, they are shoes that serve, in a very utilitarian way, the sailing crowd (Paul Sperry created them specifically to be durable and slip-resistant on a boat). But they’s also shoes that, at their core, are associated with fun—going to the beach, hanging out on a boat, summer afternoons with friends. You don’t wear them to assert your privilege at a regatta on Nantucket.
If you want to wear boat shoes and not look like a finance bro, just don’t dress like a finance bro. It’s all about making them your own. Which is actually pretty punk. After all, “there’s no punk look,” as Babenzien says. “You fucking do what you want and that’s punk.”
The whole cultural inversion thing is quite fascinating. As we’ve shown through various historical documents from the heyday, there was great anxiety about wearing the right thing and wearing it in the right way. The right way was to look WASPy. There’s still a right way to wear them, but now it’s to look anti-WASPy. In the ’80s you wore them to signal that you might attend a regatta on Nantucket. Now you wear them with a fashion twist to assure people you have no privilege, or, if you do, that you’re ashamed of it. Preppy items can be worn, but only if worn punky. This is the new authenticity.
The Sperry ad above is from 1985. As for Tucker Carlson, I went googling to see if I could find a picture of him in boat shoes. I was about to give up when one surfaced: right here on Ivy Style. Funny when that happens. — CC