How Adlai Stevenson Became an Unlikely Menswear Icon

The legacy of Boston Cracked Shoe

Adlai Stevenson
Candidate, statesman and excellent dresser.
Harry Pot/Anefo/Creative Commons
By Tobias Carroll / November 30, 2019 11:50 am

Most former presidential nominees don’t wind up as sartorial reference points — but then, most former presidential nominees aren’t Adlai Stevenson. Whether you know him from his time at the United Nations or the two races he ran against Dwight Eisenhower, Stevenson occupies a fascinating place in American history. He also inspired a pretty great Sufjan Stevens song, which is never a bad thing.

As it turns out, though, there’s another reason to be inspired by Stevenson’s life and career: the man knew how to dress.

Bill Stephenson at Ivy Style has a warmly-written look at Stevenson’s distinctive style. He also provides a good overview for what, exactly, Boston Cracked Shoe refers to, with a description of his first encounter with a Princeton graduate and investment banker in 1964. Stephenson writes 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.”

Stevenson, too, made use of this style. Stephenson cites a photo of Stevenson that ran in LIFE magazine in 1952, in which a hole in one of his shoes was visible. Stephenson notes that Stevenson was a “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.”

Stephenson makes the case that Boston Cracked Shoe depends on its wearers coming from a patrician background; essentially, it’s a matter of wearing comfortable, worn shoes because you’re in a position where you can. It brings to mind a complex overlap of style and class — and it’s led to a distinctive look that might be ready for a comeback. 

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