Don’t Miss The Boat

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.

From Esky:

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 As we’ve shown through various historical documents from the heyday, there was great anxiety about wearing the right thing and wearing it in the right way.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

35 Comments on "Don’t Miss The Boat"

  1. I still wear them – Sperry’s that is – albeit not in a “punky” way. Although any place other than a boat.

    By the way, I am a fan of Tucker Carlson too.

  2. “Finance bro” is code for Vineyard Vines.

    Polo’s punk/preppy look is as authentic as it gets. Ralph Lauren’s chino pants and flap pockets shirts (à la J.Press) scribbled with graffiti the “new authentic” as CC poetically writes. It says that you’re not one of those elitist finance frat bro douchebags who wear Vineyard Vines, but if you are, that you’re ashamed of it and are “slumming it.”

  3. Trevor Jones | August 3, 2019 at 2:47 pm |

    I’ve worn boat shoes my whole life, often in place of loafers in outfits that really should have loafers. They’re pretty comfortable, good looking, and best of all, easy. Some items come in and out of vogue but if you actually wear them regardless of the current trend, it doesn’t matter what you wear them with as they are and (theoretically) always will be yours.

  4. This touched a nerve with me.

    The quoted article can be summed up simply by telling the readers, “It’s ok to wear clothing stereotypically associated with crass shock jocks and ‘bros’ because changing the look a little means you’re not like them and therefore can feel better about yourself and the decision to wear the clothing in the first place.”

    One can get into a circular argument on what is “punk” and other discussions about personal authenticity. The writer is better off saying to readers, “Wear what you want because wearing a particular style of shoe doesn’t mean you’re a bad person – even if people you think are bad wear that look.”

    Or another way, “You wear what you want because what you wear doesn’t define who you are inside or how you treat others.”

    I wear my boat shoes because I like them. I wore them long before I learned how to sail and 20 years before Vineyard Vines was a thought. They are comfortable, hassle free, and reasonably durable (and I put mine through a lot). But I wear them in spite of the negative stereotypes perpetuated by authors who compare my look to Mr. Carlson or to “bros” because I’m confident in what I like to wear because I know who I am inside.

    If there’s any boat we should all be on board, it’s the one that stops making grand character assumptions because of how one dresses.

    Sorry for the digression.

  5. Trevor Jones | August 3, 2019 at 4:51 pm |

    @Topher, righto!

  6. whiskeydent | August 3, 2019 at 5:31 pm |

    I was wearing my (we called them) deck shoes at a fraternity-sorority mixer in 1977.

    Blond southern bell: “What’s that awful stain one your shoes?”
    The suave and debonair me: “Oh, probably fish blood.”

    BTW, I think I told that story in a previous post but couldn’t resist repeating it.

  7. They look super in their intended setting. Sailing or at the shore. Only in dark brown. Other colors and worn with a suit make me gag.

  8. NaturalShoulder | August 3, 2019 at 6:38 pm |

    I am a camp moc man myself. Got my first pair from LL Bean in 89 and they lasted 10 glorious years worn almost daily. Sadly when I tried to order a replacement pair, I learned the downside of moving production offshore. Thankfully, I have discovered Quoddy and Rancourt who make great shoes.

  9. Only sailed a little with a friend back in law school, but I’ve routinely had a pair over the years because they are truly “non-skid” on a wide variety of surfaces, and if they get wet, so what, they’re meant to. Great for a rainy day as well as a deck.

  10. elder prep | August 3, 2019 at 9:56 pm |

    I wear “boat shoes” too as they are comfortable, light weight and go well with all my summer prep wear, and I don’t own a boat. I also like Tucker Carlson.

  11. Sperry’s, original boat shoe, dark brown with laces. What’s up with the wave of anchored laces Sperry is offering? The boat shoes with elastic inside so you don’t need laces? The ability to tighten or loosen the fit is a key feature when you’re taking water over the bow! ?

  12. These journalists are fucked up in the head. The cultural revolution we’re going through is quite similar to what was happening in the Soviet Union under Stalin when people tried to look “proletarian” as it was “inappropriate” to look like an educated refined person from the middle class, as it would have you labeled “bourgeois”.

  13. “Don’t worry, I’ll hold your things, you just worry about making friends” – Cargo Shorts

  14. And just how hypocritical it is in this day and age when way too many people dress without any sign of respect towards anybody (men and women), without ANY sense of even basic shame, to label boat shoes as, somehow, “barely appropriate”, so you have to be “extra careful” when wearing them. Sickening.

  15. Old School Tie | August 4, 2019 at 4:26 am |

    I agree with Whiskeydent, we always knew them as “deck shoes”. The non-slip soles make them surprisingly useful in soggy Britain. Personally eschewed in favor of the camp moc since there is less reason to not be wearing them in town….

  16. Just how does a “finance bro” dress? Being ignorant of this species, I would love to have others here enlighten me.

  17. Sperry’s quality is low now. There was a time the shoes were well made and lasted years. Back in the day, my favorite was an oiled leather version called Kudu. I’d have those resoled multiple times before discarding them.

    Rarely do I see sailors wearing Sperry’s on boats these days. There is a multitude of well made quick-drying shoes to choose from which are far more practical then Sperry’s. See examples at

  18. whiskeydent | August 4, 2019 at 10:54 am |

    Sperry long ago quit making any that fit my stupid 14B feet, but I have found that Dunham, now owned by Rockport, makes almost identical models in my size and at a similar price point.

    I have heard a lot of complaints about the quality of today’s Sperry’s, so the Dunham’s might be superior. I wear them every day as house shoes, errand shoes, it’s raining shoes, and sometimes fishing on saltwater. Yesterday, I walked about two miles in them on errands in downtown Austin.

    I only clean them when the stains even offend me, and by then I can only make them blend in with the other blots of unknown provenance to create a patina of sorts. They blow out after about five years of my abuse.

  19. whiskeydent | August 4, 2019 at 11:12 am |

    I.T. & Don,

    Esquire’s views on menswear are centered on New York. They only venture outside the bubble to spot the next trend in NY fashion. The mag’s writers display an awful combination of smugness and ignorance. It’s best read for free at doctors’ offices and seen as parody.

  20. Been wearing them since college in the South in the early ‘80s. Digressed a few years with Bean bluchers, but wear one of the two constantly. First had Dexters, then Docksides, then a succession of Topsiders. Now wearing a blue pair with white soles from Rockport. They look great with a seersucker suit. Too casual, yes, but seersucker kind of throws caution to the wind anyway.

    To an earlier comment, hardly anything is as good quality now as it used to be, Sperry, LL Bean and, especially, Lands’ End, included. That is one reason that shirt makers such as Michael-Spencer and Mercer & Sons are true treasures. American craftsmanship which set the standard for the world. I pray they never sell their brand to corporate America or corporate anywhere else. Plus, their customer service is amazing, both Spencer Bennett and David/Serena Mercer are top notch.

    As for boat shoes, Lisa Birnbauch wrote in the preppy handbook: “The more salt stained the better.” That goes for the true boating set, but nothing wrong with land lubbers wearing them. Although, I have to admit, I enjoyed them more when I lived in Tidewater, Va than now living in Colorado.

    Finally, Tucker Carlson is a great guy in person and could set the standard for men’s dress in American in many ways.

  21. I don’t find that Sperry Top-Siders (we also called them deck shoes) are lower quality today than they were when I first started wearing them in the 70’s. I am disappointed that they seem to be made only in the DR and China, however. I understand they have or had an American made version that was made for them by Rancourt or someone.

    I continue to wear them long after my sailing days ended in the late 80’s because they are comfortable, inexpensive, fit me well, and I like the look.

  22. Tucker Carlson doesn’t seem to be wearing boat shoes in any is the pictures in the linked article. I do see Bean mocs…

  23. Caustic Man | August 4, 2019 at 3:46 pm |

    This constant clamoring for authenticity is getting rather old…

  24. Jonathan Sanders | August 5, 2019 at 9:30 am |

    I’m just impressed at how great the clothes look! The beauty of classics. And it was refreshing not seeing a skinny fit alla contemporary Polo.

  25. @Don – This is how many “Finance Bro’s” dress:

  26. Charlottesville | August 5, 2019 at 10:53 am |

    I’m not really much of a “bro,” finance or otherwise, nor am I a sailor, but I generally switch to a pair of boat shoes or camp mocs at home after work, and wear them on weekends around the house or for running errands. As noted by others, they are comfortable and can take a beating with no ill effects. Other than Bean boots for sloppy fall and winter weather, and a couple of pairs of bucks, I don’t think I have any other casual shoes (excepting penny loafers, which are not quite so informal).

  27. I have three pairs of leather Sperry Topsiders going. My favorites have been resoled three times by my excellent cobbler on Colley Ave. in Norfolk. Hit them with mink oil every so often and they will last for at least a decade. I had what my wife calls my platform Timberland moccasins resoled a few years ago and the Vibram soles are only just beginning to show wear. Were those shoes really a favorite of William F. Buckley?



  28. I don’t know if we were “signaling” anything when we wore them to school as pre-teens in the 70s and 80s, but nobody wore anything else. And, their heritage aside, they’re now just a dependable casual shoe, filling a sui generis spot in the closet between a penny loafer and maybe a canvas lace-up. But I don’t know a single sailor or fisherman who actually wears them on the boat.

  29. @sacksuit, never heard of Buckley wearing Timberland mocs, care to share your source? Just might have to get a pair now.

  30. GS

    My source was this site. Obstinately Stuck in Ivy: WFB on Clothes, 1982. I was surprised too.


  31. I’ve been wearing Topsiders since college (late 1970s). Somebody mentioned it above: we used to call them “deck shoes” in those days. I still wear Topsiders, but switched to Gold Cups a few years ago because they’re so comfortable. They are my everyday shoes and I even wear them to my office, with khakis, madras jacket, etc. I like Tucker Carlson: my wife and I watch him regularly.

  32. Terry O’Reilly | August 7, 2019 at 9:16 pm |

    I wear camp mocs and the occasional Timberland “platform” boat shoes in South Boston and in Nantucket, and have been wearing the latter style shoe since parochial school. We wore them because our moms bought them for us, and then later because we replaced the old pair with the same.
    I am an uneducated/autodidact, self-made, traditional Catholic, and take Tucker Carlson(like most television pundits) with a grain of salt. I’m into a wide variety of subcultures and their ephemeral musical soundtracks, and have never been embarrassed or aware of/afraid of any sort of “virtue signaling” or privilege malarkey.

  33. Sardonic Misanthrope | September 15, 2019 at 11:10 am |

    It is an egregious display of sophistry to assert that wealth and class are based on privilege, rather than prudent breeding and decades of responsible investments. Genes matter. The opinions of journalists do not.

  34. While in my uncle’s army, one if my tools was a combat support boat. Technically speaking I was a certified Boat Commander…captain of a lesser hull with some serious power (twin Sabre diesels). Of course it was common to violate prescribed rules like no hidden hatchet to cut the bow lines should a bridge section begin to sink and take you with it. Being a war related business as such, black leather boots were standard, no matter how dangerous for over-water wear. In the cold of winter, Germany, you could cover them with the big rubber “Mickey Mouse” overshoes which completely hid your boots. And that’s when it hit me…they could not see your Sperry’s under the Disney gear! So yes, Top Siders even saw military boat useage in at least one place in time. Mine were maple. And Bean’s heavy camp moc saw tent time at night…nothing like getting a big box with chino’s, fisherman’s sweater, and shoes delivered to you on the muddy bank of the Rhine River during a field exercise!

  35. I’m also a Tucker Carlson fan,it seems this author opened a can of worms with his tongue in cheek comments.

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