Shelby Cullom Davis (Princeton ’30) was a Bostonian of the most patrician, and endangered, variety: an Ivy Leaguer and a very succesful banker, he served eventually as ambassador to Switzerland. In dress, he favored two-button blue blazers and repp ties, khakis with cuffs, and cap-toed lace-ups cracked deeply across the front.
Ivy-Style reports that the look wasn’t confined to Ambassador Davis, either: men across New England subscribed to the Boston cracked-shoe look, wearing shoes long past the point at which they’d gone from new- to used- to battered-looking. The message inherent was three-fold: first, the men who subscribed to the look were, despite success, generally frugal and prudent. Second, they were too well-heeled and removed to be bothered with such banalities as cobblers. And finally, that their primary care was for taste, things well-used to the point of smooth burnishing, and not for high fashion.
Newly-minted lawyers and bankers climbed their respective ladders in spit-shined brogues; the old partners at the top of the ladder had the luxury of comfortable shoes. Cracked shoes meant success.
“The first time this stubborn Yankee frugality came to the attention of the public was during the 1952 presidential campaign,” wrote Ivy-Style contributor Bill Stephenson. “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 LIFE failed to note was that Adlai Ewing Stevenson II (he declined “Jr.”), scion of a wealthy family of New England politicians, was merely at ease in his own environment, cracked shoes and all. So at ease that novelist Tom Wolfe was inspired to coin, in Bonfire of The Vanities, the phrase “Boston Cracked-Shoe Look” …and it stuck.