The Great Boat Shoe Debate (and the right answer).

These boat shoes are on land.

The lead picture is boat shoes not on a boat.

Here’s Aristotle:

Aristotle did not wear boat shoes.


Aristotle knew how to frame thinking.  He wrote a book.  Rhetoric.  In Rhetoric he talked about the Rule of Three.  That people remember things most easily in three’s.  I have heard, but cannot verify, that that is why area codes and the first grouping of your phone number are three numbers.    Of course, one could argue that if Aristotle really believed his own rhetoric (see what I did there?) he would have titled his book:  Rhetoric By Aristotle.

The first pillar of the Great Boat Shoe Debate is no debate.  Yes, wear boat shoes.  Sometimes, you can get jammed up wearing them with a tie.  NEVER wear boat shoes with a suit.  ALWAYS wear a tie with a suit.  I hope that clears things up a little.

The second pillar of the Great Boat Shoe Debate is socks or no socks.  I have, as they say, evolved on the issue.  If you are on the FB group, if you know me, or even if we have met,  you know where I stand on socks.  Ridiculous.  But a thinking person can hold both sides of an argument in their head.  For example, here’s an Ivy Paul Newman actually on a boat (and before you start riffing here, boat shoes can be canvas):

Hey Heineken, I expect an ad buy.

Those are socks.  I ran through a lot of image searches.  JFK.  Socks.  Steve McQueen (who, for an Ivy guy was conspicuously boat-avoidant) – socks.  And so forth.   There is precedent here, folks, for boat shoes with socks.  As much as I don’t like it.

But you have to understand something.  On a boat, the idea is to go barefoot as much as possible.  You can start the morning in boat shoes, but as soon as possible, kick them off.  And be barefoot.  Unless you wear socks.  If you wear just socks on a boat you either (a) have never been on a boat and never want to be asked again or (b) are begging to be tossed over.

I have a theory about the whole JFK – Ivy thing.  You can’t trust pictures of JFK in casual clothes whilst he was President as Ivy touch points.   He was the President who banged up hats, and he was, also, I am guessing, the President who rarely wore what he wanted to off duty because – television.

So yes, socks if you must.  Cold fall day, you are gonna walk the dog with a cigar (for you, not the dog) and then amber-colored fluid in a glass by the fire – definitely socks with the boat shoes.  Am I right?

Which raises the final pillar of the debate.  Boat shoes if you are not on a boat.

There are, ahem, loftier-than-I fashion writers who say no.  The argument is a sound one – authenticity.   Boat shoes were designed for boats.  It’s a cool story that is offered as to the origin.  I am not so sure I buy it, but I can be convinced.  Story goes that Paul Sperry saw his dog on the ice, running well on the ice actually, and then cut slits in his shoes for traction.  I have a few problems with this story.  First, I have seen dogs on ice.  True story.  One day I was on a frozen lake.  In one hand I have my then 5 year old daughter, who was new to walking on ice.  In the other hand I have a leash attached to my new English American Coonhound, who was new to both ice and the leash.   Daughter sees a hole in the ice and goes to step in it.  Dog sees a deer on the shore and lunges for it.  At the same time.  I do a split.

Not ice but you take my point.

I, no kidding, tore my groin so bad that I almost needed surgery.  But I still have the daughter and the dog.

How’d we get there?  Dogs are by no means nimble on ice.

And that’s Exhibit A.  Exhibit B would be common sense.  Here is Paul Sperry, who looks like he spent a lot of time on the water, no?

I am with you Mr. Sperry, and I thank you for the shoes. But clearly you saw gills before you saw your dog.

Mr. Sperry clearly saw a lot of fish in his day, saw how well they breathe under water, and never thought to cut slits in the side of his, well, side.  See where I’m going with this?

With the origin story in doubt, one can reasonably argue that we can relax the standard of authenticity about boat shoes in general.   Yes, wear a tie in court.  But don’t ONLY wear a tie in court.

But if you do wear a tie in court, do it with a suit, and no boat shoes.

Problem solved.

  • JB



40 Comments on "The Great Boat Shoe Debate (and the right answer)."

  1. Unreadable.

    Try glasses? Wipe down your phone? Night school? – JB

  2. No boat shoes at the moment (tan suit, dress shoes, and tie). But later in the day once I return home and change? You bet.

    Best Regards,


  3. Boat shoes are for frat bro’s. They have no place in a grown man’s wardrobe, unless, of course, if you sail.

  4. Richard E. Press | September 7, 2021 at 10:53 am |

    Do your what to wear in court rules also apply to the defendant? If the glove don’t fit you must acquit.

  5. “Boat shoes are ugly.”: Courtney Ryan

    (Time stamp: 5:50)

  6. @EdS – “Unreadable” is harsh. I did have to jump down to the comments to take a break, though.

    @mitchell – I understand your points on both authenticity and style. To the former, it is a slippery slope to require too much authenticity when purchasing clothes. We’ll start revoking blazers from those who didn’t row for Oxford. We’ll have to ticket the Madras crowd for having never traveled to Tamil Nadu. Extend the logic too far and it’s no G&Ts for you unless you’ve mixed it from your Royal Navy rations.

    Boat shoes are a fine part of the east coast uniform. Best without socks but I’m a liberal (upholding individual liberty) when it comes to the details.

  7. Evan Everhart | September 7, 2021 at 12:41 pm |

    I accompanied someone to court a while back, I wore a Brooks navy blazer, old U.S.Army khaki trousers, a pair of Sperry 2 eyelet boatshoes, a beat up old Brooks pinpoint OCBD, and a Guardsmans tie in red and navy. My belt was alligator skin and I was a touch of very discrete white linen in my breast pocket with an old U.S. military issue leather briefcase. The desired effect was achieved and we BSed our way out of a minor issue on the other party’s supposition that I was a lawyer. Mischief managed?

  8. Yes to this. And no, boat shoes need not be confined to use on decks (how many other pieces of clothing have been adapted over the years from their original use?), but neither would you wear them on duty (see the point about suits)…unless being on duty involves working around boats. And for those who have conflated boat shoe wearing with the less-savory elements of fraternity life to the point of (unfairly) equating them, CC’s post from 2017 on the fine line between Ivy and bro culture is worth the read to recall that it has less to do with the item of clothing as it does with how you carry yourself while wearing it (and perhaps giving lie to F.E. Castleberry’s mantra that the better you dress, the worse you can behave):

  9. repptieupstateNY | September 7, 2021 at 12:59 pm |

    my teaching (history in a suburban high school) uniform: boat shoes (or Bean Blucher mocs),khakis, OCBD, repp tie; sweater and or jacket when necessary

  10. Boat shoes are frequently a go to, and (with socks) I’ve worn them with a blazer and chinos on numerous occasions.

  11. An exception to the no socks on boats rule is the rowing shell. Socks of some type are generally considered necessary while in the boat; the built-in shoes can be used by a number of oarsmen, particularly in club rowing. Socks are a bit more sanitary (think of rented bowling shoes.)
    Boat shoes make excellent dock shoes and you don’t want to pad around the boathouse in your socks. Hence, at least while on shore, boat shoes with socks.

  12. @CA: I see your point. I take things (words and clothing alike) very literally.

    There is nothing more repugnant to me than a poseur. The Ralph Lauren clothing line, Rugby, was my bete noire. It featured fake crests, insignias, and ersatz ties to clubs that never existed.

  13. Charlottesville | September 7, 2021 at 1:32 pm |

    I would call the shoes at the top “camp mocs” rather than boat shoes, but that may be simply because the darker-soled versions I bought from the LL Bean catalog in the 70s and 80s were called that. Is this a distinction without a difference?

    Sperry uses the nautical moniker, whether the shoes sport tan or white soles; I always called them Topsiders or deck shoes. My most recent pair with brown soles (from Rancourt) were called camp mocs while the virtually identical shoe with a white sole is called a boat shoe on the Rancourt website. I have been wearing both types for years, both socked and sockless and am unlikely to change now, whatever they are called.

  14. Vern Trotter | September 7, 2021 at 1:55 pm |

    “Tradition is a guide and not a jailer.”~~ Somerset Maugham

  15. My boat shoes were combat boots and black dress shoes.

  16. Boat shoes, deck shoes. To me no difference. I wear my topsiders all summer long, with chinos, jeans, and shorts. They are comfortable, light, and provide outstanding traction on wet surfaces, deck or land.

  17. Otis Brewster Hogbottom III | September 7, 2021 at 5:17 pm |

    My high school had a dress code. Sneakers (or canvas boat shoes) were not allowed. However, leather topsiders/docksides/etc were allowed.

    Also required by the dress code: socks.

    I used to wear my boat shoes everywhere, even when I lived in Manhattan for a couple years after college. Around my mid-20’s, however, I decided I needed to at least be in a beach town to wear them. So, wearing them in Newport: OK. Wearing them in the Back Bay of Boston: no.

  18. I started wearing boat shoes in the 80’s during my freshman year in college. It was my first non-sneaker everyday shoe. I couldn’t figure out whether to wear sox or not. I didn’t know about the Preppie Hand Book. This was before the inter-web so I had little to go by. At first I wore it with my white tube sox, giving me that Jerry Lewis look. Not cool, even in the 80’s. Then I wore dark gray sox. Never felt right. One day for some inexplicable reason I went sockless. It was an epiphany. I felt my life change. It was as if the fog of childhood lifted and I started seeing life differently. That day I became a man – or at least one day older than the day before. My personal bar-mitzvah. I never looked back.

  19. Chris Collins | September 7, 2021 at 9:37 pm |

    Previously I wore then around the house without socks as my house shoes. But then I bought a pair of Espadrilles in navy blue and I wear them now, but never to court or on bow-tie Tuesday.

    My sailboat is docked where on occasion and the right tides I can walk out to her, I always wear boat shoes so as to avoid cuts from the smoked oyster shells we have discarded over the years.

  20. Yes to Camp Mocs. With marled wool ragg socks. Great look.

  21. Minimalist Trad | September 8, 2021 at 12:49 am |

    @Vern Trotter,
    Many thanks for the Somerset Maugham quote:
    “Tradition is a guide and not a jailer.”
    That’s why I call my style Trad, rather than Ivy.
    Ivy was my guide; when it became my jailer, I managed to escape.
    I stick to OCBDs, but prefer non-iron shirts and lined collars. My jackets are now two-button, but I stick to navy blazers and tweeds. My trousers are chinos and grey flannels, but uncuffed. My eyeglass frames are P3, but black rather than tortoise shell.

  22. William Cochrane | September 8, 2021 at 5:05 am |

    Ahh…the eternal sock debate. It is comforting that in this highly volatile world some things remain constant. Obscure and hopelessly silly, but constant. My experience with boat shoes has been mostly sockless, as much because my blue topsiders turned my socks blue after a few minutes wearing and it was less a problem to just have my feet turn blue than to have to answer to a parent as to why I was walking across good rugs in usually soggy bluish socks when I came in (having at least the sense/survival skills necessary to kick the topsiders off at the door).

  23. “…the President who rarely wore what he wanted to off duty”

    I’ll disagree with this. Having just finished (yet another) biography of our toothy, auburn-coifed, blue eyed Irish prince, I’m 99.999 % convinced “Jack” did whatever-the-‘F’ he wanted. I’ve a working hypothesis that his behind-the-camera stylists nudged in a fashion-forward direction, and he, still a product Choatie, resisted. If anything, his choice of Chipp’s natural shoulder jacket and wool challis prints infuriated the more cosmopolitanish(less New Englandy) among his circle. The penny loafers, shetland crewnecks, and flannel pants were, I’ll suggest, JFK being authentically JFK. He wasn’t naturally populist and his contempt for camera was robust.

  24. There is an exception, I think. Reason to suppose his favorite pair of sunglasses was the Ray Ban Caravan. (Let’s recall his love of the U.S. Navy). The tortoise shell shades were probably a concession–but not to popular opinion.
    To Jackie.

  25. * of Choate

  26. addendum: Dallek’s excellent book (‘An Unfinished Life’) reveals the soul of an old-fashioned New England fogey. It’s amusing–the claim that the more sophisticated-and-cosmopolitan stake on JFK. Fiscally conservative, a Navy man but not hawkish, old fashioned Anglophile, and suspicious of reform for the sake of reform, and privately/quietly pious. He delighted in mockery of high brow culture (especially Harvard). I suspect he would’ve eaten clam chowder and apple crisp every day. Had he lived, he would’ve stuck with Chipp and resisted the 70s with all his might.

  27. First, welcome back Evan Everhart! Glad to see you again, brother.

    Second, let me take a different tack (ouch) in this conversation: I’m fortunate to live in a town where we do LOTS of sailing, and LOTS of fishing. At the risk of sounding like a jerk, here is the shoe that you see the skipper and crew wearing:–men-s-sea-kite-sailing-shoes-wide-width–P015202278

    And here is the shoe that you see first-time guests on the boat (“rail meat”) wearing:

  28. I am a long-time sufferer of Deck Shoe Authenticity Disorder. With great remorse, I admit that I have mocked landlubbing poseurs for their spotless Sperry’s that shined like a new pair of Weejuns. I opined that Topsiders should look like the ones I wore as a kid, covered in the dark stains of fish blood, grease and Dr. Pepper. You know, the manly things.

    But after 50+ years of wearing deck shoes, I have finally decided to just…give…in. Or more accurately, to just…shut…up.

    Wear’em whenever and wherever you want. You no longer need to worry about me snickering and scowling from the corner. Really. Truly. Count on it.

  29. Socks during winter. No socks summer!

  30. Never cared for them because I hate anything water-related, and it seemed just too on-the-nose East Coast preppy for a Midwestern guy. Got a pair because couldn’t think of anything else appropriate for a certain party on a hot summer day. Only wore them once, I’ll stick to minimalist sneakers in the summer.

    Has anyone else had trouble keeping the laces tied? If so, have you found a solution?

  31. I will agree with S.E. that, despite the advent of TV, JFK wore whatever he wanted as President. GHWB on the other hand, coming in a later and more intrusive age, was “forced” to make accommodations in his dress while POTUS. It was interesting and fun to watch him immediately revert, in his post-presidency, from his banal and everyman “Presidential” wear, back to his natural comfort zone of red pants, topsiders (with socks – and other items befitting of his heritage and breeding.

  32. The solution is to actually own a sailboat and wear modern boating shoes.

  33. Bill, I think your solution is the correct one.
    I felt like an idiot wearing them since I don’t sail.

    Modern boating shoes look like a good choice for walking in rainy weather.
    Thanks for spurring me to look them up.

  34. Pat McDermott | September 15, 2021 at 9:29 am |

    I used to crew on a racing sailboat, so I get grandfathered in, even though, as the line in Evita goes, “I haven’t been to sea in years”. They are comfortable, go well with jeans and shorts, and I’m old, so I don’t give a flying F what anyone else thinks.

  35. Joseph A Dougherty | September 15, 2021 at 11:16 am |

    The picture you included in this story is not Steve McQueen it’s Paul Newman. C’mon man get your iconic movie stars straight!

    Brother Joseph, um. The post says the picture is of Paul Newman. I’m all about the suggestion to make a post better, but you gotta read the post? Yes? – JB

  36. You missed the entire requirement of a decent boat shoe…….because none of you are sailors. A good boat shoe has to have 3 eyes, not 2. Two eyes wont hold the shoe sufficiently on a pitching deck. Plain and simple,…. a three eyed boat show holds the the foot securely…..a two eyed boat shoe is not a useful or decent boat shoe…. It’s a phony boat show.

  37. LOL. At two points: One. We have to still debate this. The boat shoe thing, I mean. Two. Readability. Okay, it’s readable. To a point. See what I’m doing here. Short sentences. Often incomplete sentences. (See what I’m doing here?) Telegraphic, almost. It’s sort of like reading Stein the first time. Gertrude. You know the one, Hemingway was influenced and all that. Oh, two more points, I guess: Socks. I’m not even going there. And spaces after periods. You gotta appreciate the sorta easy going approach. One space here, two or three there. Whatever works.

    I think. You might be. Getting it. – JB

  38. I’m a “no socks” kind of boat shoe wearer. I do spend most of my free summer days on a boat. However, have nothing to prove nor justify. The shoes are part of my personal style and brand. I’m seen wearing them sans socks in the winter so long as it’s not bitterly cold or there’s foul weather outside.

    I am an almost perpetual boat show wearer. On land or off, I’m seen wearing my Sperrys nearly every time I’m not wearing a tie (unless attending a ceremony at sea). I own several pairs – each with different degrees of comfort and wear that are rotated over time. New ones are worn when attending events on deck, older ones are worn in casual social settings, the best (and my favorite) are the well worn ones that I wear while sailing; they retain their function just as well as new ones.

    To me, the debate of whether one should or shouldn’t wear socks with boat shoes comes down to this: boat shoes are made to last and perform when wet. Socks, when wet, are uncomfortable and, I’d argue, unsafe at sea because they cause slippage.

    Perhaps I’m too practical or just don’t care; my GTH pants and sockless boat shoes are fine with being a little different.

  39. michael powell | October 1, 2021 at 9:10 pm |

    Got my first pair of boat shoes (Top Siders) a few days ago. It’s time for a change from deserts boots as my casual shoe of choice. I think this will look good.

  40. Terry O’Reilly | October 2, 2021 at 3:56 pm |

    @AndrewK247 Salt water keeps my boat shoe laces “tacky” enough to not come undone.

    As far as the debate of socks/sockless, boat/boatless: I’m from Central Massachusetts and always wore boat shoes or L.L. Bean type bluchers at my parochial school… had neither an issue with surly boatmen nor with gentle ribbing from other students.
    Is the wearing of boat shoes considered an affectation in some regions?

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