Immortal Sole: Adlai Stevenson and the Boston Cracked Shoe

If you don’t live on the East Coast and are under the age of 60, the term “Boston Cracked Shoe” will not likely have any resonance. But being 77, and having spent all of my business career in the East, it’s a part of the history of the Ivy League Look that is impossible to forget.

I first experienced the Boston Cracked Shoe look when I walked into the office of Shelby Cullom Davis in 1964. Mr Davis had developed a very successful business as an investment banker, and was one of the finest gentlemen that I ever knew.

He went to Princeton (class of 1930), developed a hugely successful business, and eventually served as ambassador to Switzerland. Shelby has his name on a building on the Princeton campus today. He was a traditional, old-school patrician. However, the thing that struck me when I walked into his office for the first time was that while he was well dressed in the typical Ivy look of the day, his black cap-toed shoes looked like they had been soaked in a barrel of salt water for a couple of weeks.

Shelby could have obviously bought anything he wanted at Brooks Brothers, but these were his choice for business wear.

Later I became interested in this predilection and found that, indeed, among many well bred, well educated East Coast gentlemen, many took great pride in wearing shoes that looked like they had long outlived their useful lives. In getting to know the men that subscribed to this, it seemed that it was their way of making a subtle statement about money, taste and class.

My guess is that they felt that this conveyed that although they could afford anything they wanted, basically they were frugal and unwilling to spend money frivolously — even for something as necessary as shoes. Although many of them lived rather lavish lifestyles in other areas, this small gesture sent the message that they had so much class they didn’t have to care about mundane things like shoe repair.

The junior members of a firm that were striving to climb the corporate ladder would keep their shoes well repaired and shined every day. But the guys with the Boston Cracked Shoe look didn’t worry about something like this, because they not only had climbed the ladder, they owned it.

The first time this stubborn Yankee frugality came to the attention of the public was during the 1952 presidential campaign. LIFE Magazine ran a picture of Adlai Stevenson with his feet propped on a chair, and there was a large hole in one of Stevenson’s shoes. The press was dumfounded at what they considered to be a huge faux pas.

What they didn’t realize was that Adlai Ewing Stevenson II was raised in wealthy family, came from a long line of successful politicians, graduated from Princeton, and was the member of a patrician set of men who all looked on this in a much different light than people that didn’t travel in their set.

As far as I know, the term “Boston Cracked Shoe” first appeared in print in “Bonfire of the Vanities” by Tom Wolfe. My guess is that the term was only meaningful in certain East Coast circles. I ran into it in Boston and New York, but never in any other part of the country.

Oh, and if you’re going to try this at home, bear in mind that down-at-heel shoes are patrician on Old Money types, but merely bohemian on the middle class. — BILL STEPHENSON

Pictured is a statue of Adlai Stevenson at Central Illinois Regional Airport, which includes a hole in the bottom of his left shoe.

29 Comments on "Immortal Sole: Adlai Stevenson and the Boston Cracked Shoe"

  1. Great post. I never knew that it had a Formal Name, it was just something that I have always done. .Still today you can see the the “Shoe” if you only know where to look… LOL.

    Always, Bumby

  2. Peter Carbonaro | September 15, 2010 at 6:27 pm |

    It is possible, perhaps, that Nathan is British, in which case the period could be placed outside the quotation mark and still be acceptable.

    Interesting article. I always wondered about that Adlai Stevenson photo.

  3. Mr. School: Suffice to say we’d rather look at the bottom of Stevenson’s shoes rather than old Adlai himself.

    Mr. Carbonaro: Nathan’s correct use of the colon suggests he knows a thing or two about punctuation, and certainly to place the period outside the last quotation mark. Heavens, man, is nothing sacred anymore?

    As for the cracked-shoe philosophy, I’ve noted a similar thing from time-to-time in actual clothing worn by men who are not lacking means to buy new clothing, yet wear shirts and jackets with severely frayed and nearly torn collars and cuffs, acting like they either never notice or can’t be bothered by it.

  4. Bill Stephenson | September 16, 2010 at 2:42 am |

    Excellent photo, Old School. It gets to the point that here is a gentleman, very well dressed: grey three piece suit, tasteful checked shirt, tie that blends perfectly with suit and shirt, perfect dimple in the tie, topped off with a collar pin. He obviously put things together precisely as he intended, including the shoes.

    If we could see the shoes that he was wearing in that photo on the LIFE cover, they would probably look much like the ones in the photo of Stevenson seated, and photo of the statue, that Christian found.

    The LIFE cover that you posted, and the ones that Christian found seem to have Stevenson saying, in effect; “I know exactly what I am up to, and it works for me, and my peers, but don’t try this at home.”

  5. OK…

    I’ve always been partial to the ivy/preppie/conservative asthetic. Something about its association with New England frugality and the Pilgrim way appeals to me. I get that part of it. But this idea of intentionally walking around with holes in the soles of your shoes is just a bit much. If a shoe has a hole in the sole, it has lost a major portion of it’s utility…mainly keeping your feet protected from the elements…that’s just common sense, another fine New England trait.

    The Boston Cracked Shoe crowd may think it’s beneath them to think of such mundane matters, but out in “reality”, most folks who see something like this and find out the effect is intentional might think twice about the person. Frugality is admirable…but this crosses the line into gentle eccentricity. No wonder Stevenson was never elected President! How could he have protected the free world if he couldn’t take the time to protect his own feet?

  6. SnowHillPond wrote:

    “Frugality is admirable…but this crosses the line into gentle eccentricity.”

    Absolutely agreed. I’ll take it one further: it crosses the line into gentle affectation.

  7. Ruben Henriquez | September 16, 2010 at 8:15 am |

    This post is incredibly similar to this post, posted the next day…

  8. All of it describes the typical New England Yankee: cracked shoes with holes, brown shoes with navy suits, (his father’s suits) high water pants, frayed shirts and bow ties, worn out brief cases, lock jaw pronunciation, wooden boats, bad backs, ugly women, bad teeth, and thinks tipping is a city in China after chowder at Locke-Ober.

    Describes half the people I know in Boston whose grandchildren now cannot get in to Harvard in spite of the buildings in their name.

  9. Peter Carbonaro | September 16, 2010 at 11:32 am |

    Mr. Rahman, agreed. You obviously know that while quotation placement in American English is dictated by hard and fast rules, British English adopts a more functional approach to quotation placement. Thanks for your support — Henry Watson Fowler would be proud.

    Regarding the intentially frayed and cracked look, I had long thought that the sales staff at J. Press were underpaid and couldn’t afford replacement wardrobes. You’re too kind when you call it “gentle” affectation; it’s downright contrived.

  10. The cracked shoe is probably the diametric opposite of all the modern Harvard MBA trash with cash who ruined the economy. I’ll take a cracked shoe affectation over a cracked nation affectation any day of the week.

  11. John Grisham is the exact same way. I saw him the other day at a formal event and he had on a nice blue suit……with beat to hell light brown cap toe shoes. I get what he is doing…he has 90 million bucks but loves his shoes. It must be a rich person thing.

  12. Jim Donaldson | September 16, 2010 at 4:10 pm |

    Plus one other thing: clothes (and shoes) are always closest to perfection (comfort, drape) the moments right before they completely disintegrate. One’s favorite clothes are usually the ones that really should have been disposed of because they are worn out, but you can’t bear to do it.

  13. “True Prep” = Godfather III

  14. There is a piece in today’s NY Post about Mayor Bloomberg wearing the same two pairs of loafers for over 10 years. I always thought he was well dressed; now we know he wears loafers with suits. Back to the subject at hand, as a young lad I knew Gov. Stevenson slightly, even as he was a political enemy of my maternal grandfather. He was always a fastidious dresser; I do not group him with the Swamp Yankees I described above and so well chronicled by John P. Marquand.

    My own Boston Cracked Shoe was bought at Church’s on Boyleston street some 25 years ago, a black cap toe that cracked slightly at the bend but was fine for 20 years. They seemed to disintegrate all at once, much as did the One Horse Shay. Church’s since has new ownership and has gone to hell.

  15. Kenneth Seward | November 4, 2010 at 2:03 pm |

    I was just watching Robert Altman’s ‘Health’ and there was a reference to a hole in Adlai Stevenson’s shoe… and this is where I ended up looking for an answer. Interesting to find out that it’s something of a tradition and not isolated to that one iconic image.

  16. Douglas Korves | May 11, 2013 at 6:31 am |

    I cleaned out the closet of my brother-in-law who sold shoes at Macy’s between jobs in banking. He had a pair of plain capped Allen Edmunds that I watched him wear for 10-15 years. I claimed them and wore them another 10 years. They would get dirty and salty but always shined up.
    I gave up on them when the creases behind the caps opened up.

    I also bought a pair if real cordovan loafers at Brooks Bros for $42 in 1969. I wore those for 25 years before the stretched and settled into the ground. I think they cost $475 today. Of course I was making good money then $110 per week.

  17. Jeremy Pollack | August 1, 2013 at 8:15 pm |

    Some 5-10 yrs ago now, Princeton University Library had a Stevenson related exhibit (NB: Stevenson gave his papers to PU). At the exhibit a campaign-era song was played, ‘There goes the man with a hole in his shoe’. Have you heard the song or know where it might be on-line? thx

  18. The Boston cracked shoe is usually bespoke and is cracked by many years of polishing. It is always polished and never run down. Just cracked.

  19. Wearing old shoes or other items to the point of them being past their prime isn’t necessarily about thrift or any kind of patrician outlook. I think it exists in many different forms and contexts. It can quite simply be because a wearer doesn’t want to depart with beloved items, which become familiar and like old friends, perhaps because their style or fit is no longer available. In addition, many men, unlike those most likely to be on this site, have traditionally not enjoyed shopping for clothes. That is likely why Brooks ready-to-wear was actually appealing to many men because it was less of a hassle.

  20. Ah, Bloomington-Normal International. . . We know the airport well. Not many men in the area look as pulled together as the statue anymore. Just three hours from Chicago, but might as well be on the dark side of Pluto. We used to live next door to the old Adlai Stevenson house on McLean Avenue just across the street from McClean Park before escaping to the greener, snowier environs of Michigan.

  21. Did anyone consider that he was just campaigaining and did not get to the cobbler?,rather than an intentional look. I would think having water seep in your shoes would be uncomfortable.

  22. I can think of at least three reasons to wear aged shoes: 1. to affect what you have just described for social reasons; 2. because prefer the look and aesthetic of worn-in clothes to new or shiny ones; and 3. because you don’t care enough or have the money to replace your shoes. The first relates to some yankee descendants’ self-conception and attempt at identity–the attempt to make a social marker out of aspects of family and social history. In short, the lifting up of certain attitudes and values thought to be puritanical or yankee as markers of social distinction. (This relates to the glorification of thrift, for example, as a puritan-yankee virtue, whereas the opposite was quite the case among, say, aesthetes at English public schools in the mold of Evelyn Waugh). The third reason is most authentic and perhaps why many men wore shoes as they did; they didn’t think their shoes needed replacing because lots of others did it too. Or they were like most men in relation to clothes and didn’t notice much at all. To put the second reason in a larger context, who from anywhere doesn’t think a leather duffel or many other items looks better once at least broken in? Or baseball glove! So the point of all of this would be that The Boston Cracked Shoe look is an artificial construction that is being imposed on the subject matter in ways that are limiting; so while it is important to understand this history it’s also important to contextualize it more broadly.

  23. Frayed, torn or discolored shirts should not be worn by anyone not totally destitute.

  24. Re: crepes suzette

    there are many in the upper and upper middle classes who would consider the appellation ‘bohemian’ quite a welcome achievement

  25. “A tear is unfortunate, but a stain is a vice.” — Balzac

  26. depends on what tears

  27. One element that isn’t noted in the piece was that of comfort. Before the introduction of Rockports and other comfort-first footwear, having shoes that were comfortable was a priority. But they had to be polished.

  28. Vern Trotter | January 23, 2021 at 12:19 am |

    Adlai was very parsimonious; he was cheap! He had a whole stable of wealthy, mostly married girlfriends, who picked up his checks. One of the last, the day he died on a London sidewalk, was for the last six years, Marietta Tree, wife of the English gentleman, Ronald Tree, grandson of Marshall Field. Marietta was the granddaughter of The Rev. Endicott “Cotty” Peabody, Rector of Groton. Marietta organized an advertisement in the New York Times proclaiming one thousand Women for Stevenson while he was running for president. Wealthy husbands around the country took notice when they saw their wives’ name.

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