Jeb Bush’s Taped Shoe Might Be the Ultimate WASP Fashion Flex

By Jennings Brown

The 2016 campaign trail is a runway. Donald Trump had his own fashion collection. Ben Carson’s signature power pin-stripe suits are the loudest thing about him. Marco Rubio isn’t ashamed to wear high heels. And, of course Hilary Clinton has made the pantsuit so iconic that Lady Gaga now prefers them over raw meat and bubble wrap. But it seems Jeb Bush has been the true fashionisto all along.

Yesterday, New York Daily News’ Adam Edelmen suggested that the Florida governor’s shoes are deteriorating almost as fast as his presidential aspirations and brought attention to a photo of Bush at a town hall in Nashua, New Hampshire, wearing cap-toes held together with grey tape. Since then, many fashion police have taken to social media to poke fun of his footwear.

None of them seem to be aware of a classic prepster look known as the “Boston Cracked Shoe.” Worn by New England elites, the Boston Cracked Shoe express a sense of give-no-fucks tenacity, similarly conveyed by that icon of prep style known as “go to hell pants.” Tom Wolfe used the phrase in “Bonfire of the Vanities” to describe protagonist Sherman McCoy’s footwear, but the trend has been around much longer.

While most probably think Bush is neglecting his kicks, he could actually be channeling his Massachusetts prep school days. “The Official Preppy Handbook” even notes that wrapping old shoes in tape is a functional way a bit of flair. Besides, all the Bushes are longtime heroes of Trad style.

In an article about the Boston Cracked Shoe, Ivy Style writer Bill Stephenson recalls another instance when a presidential candidate was chastised for for his frugal footwear. Adlai Stevenson II had just won the Democratic nomination in 1952, when a Michigan newspaper photographer took a photo of the Illinois governor and Princeton alum writing a speech and wearing tattered shoes. The image, which would later win a Pulitzer, shocked many Americans who couldn’t believe a man running for president didn’t take better care of his attire. But Stevenson’s campaign embraced the scrappy look—which added a dash of everyman to the East Coast upper-cruster—and even gave out pins and shirts with a well-worn shoe sole.

Of course, it wasn’t enough to seal the election. Stevenson lost (twice) to Dwight D. Eisenhower, a military man who no-doubt took very good care of his shoes.

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