Post Covid Chic—Boat Shoes are Back

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According to recent stories in the New York Times and NPR all bets are off when it comes to fashion. In essence, the fashion police have given us license to wear whatever we please. As if we need the Times or NPR to tell us how to dress. Truth is, after a year or so of isolation, people are simply doing their own thing.

The recent gyrations in the fashion industry have been historical.


A recent Fast Company article reported that during the Covid era, industry revenues dropped about one third of 2019 numbers.

There was an exception.

Consumers actually increased spending on “casual” and “active” wear. And why not? People were not attending business meetings in the flesh. They were present at zoom meetings, so they didn’t have to impress the boss or client with their fabulous wardrobe.

Ergo, what folks wanted from clothing was comfort and utility. You didn’t have to go overboard on high end stuff, so long as you looked decent enough on your monthly pilgrimage to Costco.

Do you or don’t you wear socks with boat shoes? In Hawaii no one would even think twice about it…

Now that we are making our way out of confinement, we can start paying more attention to re-creating our own style. In past columns I’ve focused on “Covid Wear” — particularly trousers and crossover gear that works for the outdoors or our self imposed, semi-solitary confinement.

Given that we’re socializing it’s time look at footwear, specifically shoes germane to Hawaii.

This is a place where people wear slippers (or slippahs in local parlance) and being seen with socks and shoes is not particularly cool for your personal brand.

That’s when it dawned on me, boat shoes make a lot of sense. These are the only shoes I’m aware of where it’s definitely not cool to wear socks.

Just ask the epitome of style, John Legend.

This guy, lost in thought, has the right idea.

In addition to being an Emmy-award winning performer and, a social activist, Legend has been a global brand ambassador for the legendary shoe manufacturer, Sperry, since last year. He’s popping everywhere on Sperry’s marketing campaigns and in their social media content. He’s also collaborating on a new fashion line of shoes (including boat shoes) which come out later this year. Yes, my eyes are peeled.

There’s some irony here.

Boat shoes are timeless fashion indeed, but their origins are in the WASPY, 1930s epicenter of yachting—the Cruising Club of America. (We’re not talking gay bars).

There was a need for sturdy shoes with rubber soles that wouldn’t slip “topside”. This was purely pragmatic. No fun breaking your leg or whacking your head on the mast or a stanchion much less, going overboard. That’s why the original boat shoes were so popular.

Boat shoes were designed for a reason by the founder, Paul Sperry. I can tell you from personal experience, slipping on a deck can be treacherous. Mr. Sperry’s boat shoes were the perfect solution.

On a serious note, the “Sperry” soles (used on boots) were even part of the WWII effort to keep sailors safe on deck.

It’s been way over half a century since members of the New York Yacht Club were the only ones that donned boat shoes. Like a lot of practical, durable items—think Ben Davis workpants, bib overalls, etc., boat shoes became a fashion statement among young people.

Of course, they are still are standard wear for serious sailors and (perhaps) preppies (if they still exist.) Notwithstanding their establishment lineage, boat shoes are now unequivocally hip. (Ask John Legend if you have any doubt).

For you anti-establishment types, the Preppy thing might be off-putting but I say be open minded. These shoes transcend space, time and class.

Or as the Sperry folks say, “the brand is now fully rooted in the history of American style”. 

Given our proclivity in Hawaii to shun socks, we don’t need to be reminded that it’s cool to wear boat shoes sockless. However, for folks on the mainland who might be insecure about these things, New York Times bestselling author (of Men and Style), David Coggins, proclaims: 

“We can’t have our feet shackled with grotesque tube socks, corseted and constrained. Go forth with a liberated ankle!… 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…”  

Modeling my “Amaretto” Sperry Gold Cup shoes at sunset in Honolulu

Suffice it to say, Mr. Coggins is preaching to the Hawaii Choir.

According to a press release from Sperry, John Legend himself threw down the style gauntlet, stepping out in his cropped trousers and boat shoes, asserting his bare ankles. Said Legend of the age old socks-or-no-socks question, “It depends on the cut and fit of your pants, and how cool you are”.

I think in Hawaii it’s safe to say, we’re pretty darn cool when it comes to fashion.

Sperry Boat Shoes come in a variety of styles and price points ranging from about $95 for the entry level Men’s Boat Essentials to the Gold Cup series which can run up to $374 if you go for their Handcrafted in Main category. I opted for mid-priced Gold Cups (made outside the US) that sport the Anti-Shock and Vibration (ASV) technology soles with enhanced traction and removable molded EVA midsole provide shock absorption. They run $179.

Anti-Shock and Vibration technology soles are the way to go on the Gold Cup series.

They are perfect for my Hawaii lifestyle. They are really soft and comfy to wear. The leather used in the Gold Cup style is a better grade and hence, they feel better. I noted that the sockless break-in time was not long at all. They were flat out comfortable from the get go.

What’s practical for me was how they’ll go with just about everything.

You can wear them with jeans, technical pants, shorts–even with a blazer if you want to get formal. (They are probably not the best for hiking but you could still do it).

I liked the thoughtful video from Parker York Smith (below) who has some good ideas of how these shoes can work for you. (Granted, this guy is from the Mainland and clearly is preppy material but he seems ok and has nice abs).

I plan to wear them at an upcoming birthday BBQ and who knows, maybe at the next Chamber of Commerce meeting.

If you have any personal experiences with boat shoes drop me a line!

Robert F. Kay is a columnist for the Honolulu Star Advertiser, a health nut, the author of two Lonely Planet guidebooks and (He appreciates a good pair of boat shoes).




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