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Free the ankle! Aniyah Morinia, Laura Kaupke, and David Coggins are for a liberated ankle, and we wanted to find out why.

#SperrySockDebate (1)

Before I get into the whole socks-and-boat-shoes debate, I’d like to start with a disclaimer: When it comes to fashion choices, I’m not one to judge. I’m a fashion editor, so it’s literally in my job description to test new trends and stay open to unpredictable styles. I mean, what’s fashion without a little controversial dressing? But even I have to draw the line somewhere. And having been born and raised in the Sunshine State, where boat shoes are a year-round staple (and dare I say necessity), I couldn’t not speak up for all the boat-shoe veterans out there who are rightfully confused about the addition of socks to this equation. Look, math is not my forte, but socks and boat shoes simply don’t add up. I like to think of the boat shoe as the warm-weather cousin of the loafer and the casual, shoreline alternative to the slip-on, and wearing socks on an 80-degree day by the water is just wrong. Wet socks are an absolute nightmare, and no fashion trend on earth could convince me otherwise. I mean, it’s 20 degrees in NYC right now, but the thought of wearing socks with my Sperry boat shoes is giving me cold sweats. So if for no other reason than to close this bizarre chapter of fashion and put my mind at ease, I’m staying proudly on #TeamNoSocks.

— Aniyah Morinia, @aniyahmorinia

Aniyah Morinia is the Associate Editor of Branded Content for Who What Wear.



In all actuality, I’m a “sometimes socks” kind of gal, but in a pragmatic sense. Always with boots—I’m not insane. Occasionally with sandals—hey, it’s a ~vibe~. And consistently with sneakers, but the no-show kind—it keeps the mystery alive. However, when it comes to boat shoes, I’m a total newb. With my first pair, I’d assumed a thin layer between my feet and foamy insoles would be my comfort zone based on my usual preferences. In fact, I admire sock flair on so many. Classic white tube socks in all their glory, the subtle flash of a patterned dress sock peeking from trouser hems, or an unexpected flash of neon covering attention-seeking ankles—great fun. But the moment I slipped my bare feet into a classic pair of topsiders for a try-on, it became clear—team “no socks” for this girl. Praytell the uncharacteristic choice, you ask? It’s all in the cushy and breathable feel of the shoe.

Firstly, I was awed by the featherlight feel of the mocassin design. For whatever reason, I expected something weightier. Then, I noted how well the boat shoe started molding to my feet with a few steps—what sorcery is this? I wondered. Finally, due to the appropriately-snug fit, it occurred to me how bulky a sock would feel in the mix. Hard pass on that—I’ll risk a quick shiver should a cool breeze pass by. So, with that, I still fall in the “sometimes socks” camp. But when it comes to boat shoes, consider me a steadfastly “no socks” team member.

—Laura Lajiness Kaupke, @lauralajiness

Laura Lajiness Kaupke is a freelance writer and editor covering fashion, accessories, fine jewelry, and lifestyle topics. She currently resides in Denver, CO after 12 years in New York City with her husband and rescue chihuahua mix, Bingham Eugene.


“Boat shoes mean escape. We leave our responsibilities on shore and set off on the high seas (or the quiet lake) and are truly at leisure. We step onto the deck of a yacht (or the yacht of our imagination) with an air of studied nonchalance.

More likely it’s a little Sunfish, but that’s alright! What else do we leave behind as the wind fills our sails? Our socks, of course. We can’t have our feet shackled with grotesque tube socks, corseted and constrained. Go forth with a liberated ankle!

What about back on solid ground? Again sock-free is the solution. It’s really a state of mind and an empowered one. A boat shoe communicates its wearer’s relaxed nature, a personality that does not conform to a rigorous office dress code.

In a boat shoe every day feels like Saturday, work far from your mind. Ideally, you’ll be out of reception, unreachable by bosses, in-laws and creditors.

Socks still have a place in life. They should be reserved for a meal where the restaurant has a wine list running north of ten pages, which you peruse while wearing a coat and tie. Or as you settle into your box at the opera, and get comfortable for a four-hour performance.

Those are rarefied situations indeed. And good ones to look forward to. The rest of the time wear boat shoes the way God intended: Out and about and against your skin.

— David Coggins, @davidrcoggins

David Coggins is the author of the New York Times bestseller Men and Style. He has written about style, design, and manners for numerous publications, including Esquire and the Wall Street Journal. He is a contributing editor at Condé Nast Traveler and lives in New York City.

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