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

Seventy-seven-year-old Bill Stephenson graduated from the University of Oklahoma in 1954. After serving in the Air Force, he spent 40 years in the insurance industry, including acting as executive vice president of Fidelity Union Life. He presently resides in Princeton, NJ, and frequently audits courses at the university. He was recently appointed Ivy-Style.com’s Elder Statesman.

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