Cracked Shoes And Old Clothes


Yesterday on Ivy’s Facebook group much fun was had over a Daily News article about Jeb Bush, who was spotted with a piece of duct tape holding his shoes together. Nobody at the paper, or in the readership, know where that comes from, but for Tradsville it’s probably Bush’s most Old Money gesture in the history of his faltering presidential run.

There’s a long history of politicians with decrepit footwear from the campaign trail, with Adlai Stevenson the most famous. Eventually this became known as the Boston Cracked Shoe look.

My own experience with the look was a Baby Boomer-era guy from Pasadena who actually walked around with duct tape holding his Weejuns together. And I thought that was only a legend.

This leads us into a piece a reader alerted me to back in December. It’s an article in the Telegraph called “Why won’t men throw away their old clothes?” Author Rowan Pelling writes:

I am endlessly touched by men’s sentimental attachment to old clothes: Shetland jumpers that are more hole than whole, Panama hats missing half the crown, shirts with collars so frayed you can plait the edges. One barrister friend, who’s just turned 50, has been wearing the same leather jacket since his student days. No matter that, nowadays, he’s more Sid James than James Dean.

Check out the full story here, which has photos of Prince Charles looking like a tatterdemalion. — CC

34 Comments on "Cracked Shoes And Old Clothes"

  1. As anyone who wears traditional “gunboat” shoes can attest, there is something more than just yankee frugality to allowing leather brogues to reach tattered status. The traditional long-wing with full heel and soles is exceedingly stiff as a new shoe. This is in contrast to softer leather walkers or gum shoes customarily worn by cops or dept. store clerks. Allowing the shoe to cure and conform to your feet over months and years will eventually make the thick leather supple in much the same way as a baseball glove. Even applying polish can make the curing time longer, and re-soling means you might have to start all over again, so you just wore them without doing any maintenance while confident that they would practically never wear out. The result is ultimately worthwhile as you acquire an almost customized comfort and longest lasting shoe. I still wear pairs that I purchased 40 years ago. The 1950’s gunboat shoe, invented in Wisconsin (like the Weejun), was initially popular among Midwest bankers and lawyers, but in the post-war era quickly became an eastern establishment white collar status symbol. As shoes (and clothes in general) became more comfortable in the 1970’s, I think younger men became less willing to wear shoes that required “curing” to reach ultimate comfort. In my generation, the man in well worn shoes was once seen as a practical, patient and dedicated company man. I think that perspective may be lost a bit today.

  2. Charlottesville | February 9, 2016 at 3:30 pm |

    Nice post, Christian. Tape on Weejuns and topsiders was certainly a familiar sight when I was younger. I am a minor exemplar of the ragamuffin look still, but more driven by laziness and tightwadery than old money connections. I had the linings on a few winter suits refurbished at the end of last winter, but mostly I am sorry to say that I tend to let my wardrobe sink gradually into decrepitude. I have at least 3 tweed sacks from BB and Press that badly need to be relined, but the holes don’t show on the outside and so I keep wearing them. I vacillate as to whether double soled cordovans need to be repaired when only the first sole is worn through. The hole is visible if I cross my legs, but I wore then yesterday, and they didn’t leak so resoling seems a bit extravagant. Otherwise, what is the point of double soles? My hats vary from looking more or less like new, to rather battered, stained and, in at least one case, hole-ridden. And yet, like the frayed OCBDs and holey khakis in my closet, I hang on to them all. While I lived outside of Boston for a few years long ago, I think the trait comes more from my Virginia mother than my Yankee sojourn.

  3. Frugality is not just an old-money virtue.

  4. I think a part of it is viewing certain items of clothing (sweaters, overcoats) as “gear” rather than “fashion”. For example, Prince Charles’ much mended Barbour still keeps the wind and water out, is going to be worn when doing something in the outdoors, so he sees no need to replace it: It still works. My ten-or-more-year-old rust heather lambswool sweater has some mends (not reweaving) but it’s light and warm and it still fits

    Plus, I think “our type” of clothes buyers spend time, effort, and decent money to get something that WE think is right, and have a sneaking feeling that if we toss it when it shows some age we’re not going to find a suitable replacement these days for any reasonable price.

  5. Ward Wickers | February 9, 2016 at 5:38 pm |

    I have lots of clothes that are frayed, worn out, and just beat. An old LL Bean Norwegian sweater with holes and pulls, a few torn and frayed Patagonia flannel shirts, an old, randomly patched Filson Tin Cloth field jacket, and more. I still wear them. I buy stuff I know will last. A few holes and tears are expected. I wouldn’t get rid of them because of that. Besides, I like those clothes.

    When the dogs won’t walk with me unless I change into something less tattered, I know it’s time to let the piece go. It then has a new life as a rag. And, I’ve had rags for a very long time, too.

  6. I believe the origins for such practices stem from Great Britain. You might say keeping an item forever is a national pastime and not restricted to clothing. It’s cars, appliances, etc, as well. If it’s repairable, they will repair it!! Not sure that duct tape is part of their repair kit?

  7. Marc Chevalier | February 9, 2016 at 8:13 pm |

    Duct tape: homely stuff. On leather shoes, it’s ugly in a showy, obnoxious, GTH way.

    If duct tape is the only adhesive that can hold one’s failing shoe together, then it’s time to drag the old thing to a cobbler.

  8. I feel guilty when I’ve reached the point where I have to discard something. Even then it’ll be moved to purgatory.

  9. Had a Pendelton herringbone western style jacket that I loved more than life itself in 1982. But I “out-grew” it, so to speak, and gave it to my slimmer, more active brother, fully expecting that he would appreciate it for the gem it was, wear it proudly for many years, and take care of it. That was a flawed hope. We invest a part of ourselves in our choices; indeed, our choices are reflections of our personality, values, and inner nature. To toss something — a mirror of our souls — is painful. That might be one reason we hold on to things. Just one fellow’s impromptu take.

  10. Pend-LE-ton…my bad.

  11. Not polishing shoes to help them mould to your feet? Ridiculous.

  12. Bags' Groove | February 10, 2016 at 4:35 am |

    @M Arthur
    Old GB, post war rationing and make-do, yes, but not today’s GB. I’ve never seen any sort of tape on a once-good pair of shoes, either as a kid or adult.
    My clothes repairs have been a little more subtle. My 70s Barbour recently came back from having the insides of its sleeves replaced, and my ancient and much-loved leather jacket just returned from being relined. Prior to that the lining had been in rags for far too long, much to my wife’s disgust.
    I thought this Boston cracked business really only referred to uppers. The only shoes I’ve worn to the cracking stage were a pair of Church’s Consuls. I foolishly threw them out, and regretted it almost immediately.

  13. Loafer Lawyer | February 10, 2016 at 9:19 am |

    Currently, my most treasured weekend attire is a pair of LL Bean Khakis whose cuffs are tattered and frayed to the point of being stringy, a blue OCBD from Jos. A. Banks, with split cloth at the tip of the cuff and holes in the outer layer of the neck, and rubber soled Johnson & Murphys, where the sole is separating and probably no more than weeks from flopping around a bit. There all worn in, have conformed to my shape, and are comforting. Even with the LL Bean “guarantee” I’m not much interested in letting items so comfortable be replaced. Or, maybe JEB is just channeling his boarding school days in a neighboring state.

  14. Loafer Lawyer | February 10, 2016 at 9:21 am |

    They are… uggh, Seven years of post-secondary education down the drain.

  15. @Mr Brown
    Not polishing shoes to help them mould to your feet? Ridiculous.

    Maybe this is a generational thing. I can remember a time when shoe polish was unavailable due to rationing.

  16. An old girlfriend gave me a Harvard sweatshirt back in the mid eighties. The love affair with the girl lasted a couple of years but I still love the sweatshirt. The garment may dissolve to dust any moment but it is one of my favorite things. Hey, maybe I could use duct tape.

    I did not attend Harvard. To wear the garment is bad form, I know, but it was a gift from a Harvard student.

    Mea culpa

  17. Prince Charles’ worn-out antique clothing has been written about at length previously

  18. “Clothes that never went out of fashion because they were never in fashion. Clothes that are over and above fashion – and which he is thus happy to wear for decades on end, repairing them as and when necessary.”

    That’s beautiful. I am inspired.

  19. @ sacksuit

    No worries. A gift from an old girlfriend is treasured ware in the grand prep/trad tradition almost as much as swiping clothing from a frat brother or a hand-me-down from dad. It’s the story that’s key. Would only be better if it were from an all girl’s school.

  20. 7 years ago I was gifted a pair of Cole Haans. 2 weeks ago they started coming apart and I wear them with no compunction. The wife is consistently forcing me to make SA runs.

  21. @taz

    I was expecting to be excoriated for wearing such a garment by a the trad community. At least the embroidered Harvard University script is small on the left chest and not emblazoned across the entire front of the garment. After the shirt finally disintegrates, or the wife discovers its origin, it will be my only connection to the venerable institution.


  22. Ward Wickers | February 11, 2016 at 7:40 am |

    Not polishing shoes to help them mold to your feet … I kinda like this. It’s a good excuse to avoid polishing. A lazy man’s trad.

  23. The odd treasures. A patch madras sports jacket from Joseph Banks bought in 1981 now three sizes too small. Hey when my dad got old and ill he had to have things taken in. I’m set. A pair of British tan Florsheim Imperials from 1974 ($48) that I show off to young female attorneys whose mothers were barely alive when I bought them.
    I just know they find that fascinating.

  24. I often have my gentleman’s personal gentleman wear my clothes for six months before I wear them.

  25. Marc Chevalier | February 11, 2016 at 1:06 pm |

    It’s a male Trad “thing”. Post-collegiate Muffys have the good sense to not sport duct tape on their loafers.

  26. Henry Contestwinner | February 11, 2016 at 6:44 pm |

    This is an interesting parallel to the Japanese wabi-sabi esthetic,* in which the old, the worn, and the cracked are valued, because they are imperfect.

    It seems to me that the appreciation of cracked shoes and old clothes, wabi-sabi, and vegetarianism and other forms of voluntary dietary restriction, are found only in (sub-)societies of plenty. It’s stylish when Alan Flusser wears a $125 Seiko; not so much when we plebes do. A millionaire driving a a late-model American car is admired; a working schlub driving the same car just can’t afford anything nicer. DINKs with three stalks of asparagus on their plate for dinner—and little else—are refined; a grad student who skips lunch and has salad for dinner because that’s all he has money for is just poor. And so on.

    *Christian’s favorite word.

  27. Isn’t there an old saying about seersucker that you need to be rich to wear cheap clothes?

  28. Henry Contestwinner | February 11, 2016 at 11:49 pm |

    Perhaps; the saying escapes me at the moment. As I recall, the story goes that seersucker suits were considered poor men’s clothes until somebody with money noticed that seersucker was a lot more comfortable than wool on hot, humid days. Richie Rich showed off his comfy duds to his friends, and a summer classic was born.

  29. A tweet from me and an old post from a contributor get picked up:

  30. Duct tape on boat shoes or espadrills, fine, on loafers, not fine.

  31. My attorney wears BB shirts that are fraying around the collar. It used to upset me before I realized through this blog that it’s a source of pride. His shirts must be well 20+ years old. It’s not about money – he has plenty of money.

  32. All sports professionnels ont été interdits à Cuba depuis plus de cinq decades.

  33. Arthur McLean | June 27, 2020 at 7:06 pm |

    Does anyone anymore have their collars turned when they show wear on one side?

    Wear tweed. It lasts forever. Had a favorite sportcoat from the Saks U. store in Princeton. Expensive!!! (wrote a hot check for it which dad covered) but it lasted 1960-1988. Proved to be a bargain.

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