Why Are Rich Guys So Obsessed With These Boring-Looking Shoes?

Recently, I’ve observed a similar shoe surge, this time, of Loro Piana’s minimalistic Open Walk slip ons, which the brand has sold since 2005, but for many reasons seem to have soared in popularity of late. They’re tough to describe: Though the sole is white and rubber like a sneaker’s, the upper is supple and a bit chiseled, recalling an Italian Chukka boot. (Loro Piana is based in Milan, Italy.) Suede Open Walks retail for $1,050, and a pair in deerskin will chomp $2,425 out of your checking account. Their more-loafery sibling, the Summer Walk, recalls laceless Sperry boat shoes—but cost $995 in leather, roughly ten times as much (and $875 in suede). (Through a representative, the brand declined a request for an interview.) 

Those lofty prices probably go a long way toward weeding out buyers who don’t make an annual pilgrimage to Davos. Open Walk-shod men in the wild often wear them with starched khakis and some kind of cream sweater. In short, they look rich. Jerry Lorenzo, the raffish designer of Los Angeles luxury label Fear of God, has worn Summer Walks with camel-hair overcoats that evoke the wardrobe of Richard Gere’s well-heeled character in “American Gigolo.” And the shoes have never looked more at home than when gazillionaire character Kendall Roy, in the most recent season of HBO’s money-mad family drama “Succession,” wore them to a wedding at a palatial Italian villa. 

“I call it the Russian oligarch’s shoe,” said Michael Martin, 31, a mortgage banker in Portland, Ore., who, though neither Russian nor an oil baron, owns nine pairs of Open Walks. “The majority of people that I’ve seen that wear Loros are extremely wealthy. I see people wearing it, I know that they have good taste,” he said, offering a self-flattering assessment of the shoe’s fan base. It should be noted that the brand has deliberately pushed the shoes harder in recent years, perhaps swaying consumer tastes. It opened temporary stores dedicated to the designs in 2019 and ‘20 in locations like New York’s Meatpacking District and Hong Kong. 

If indeed, as Mr. Martin suggests, “Loros” are the answer to the question: “What shoes are wealthy men spending their money on right now,” the answer would have been quite different decades ago, when well-off corporate-types almost universally favored traditional leather dress shoes. In the (now cringingly dated) 1988 manual “John T. Molloy’s New Dress for Success,” the author notes that “the wing tip and other plain lace-up shoes are the traditional footwear of the American businessman,” and that loafers are suitable only “if they are dressy and obviously expensive.” As recently as 2007, the “Details: Men’s Style Manual,” a bro-y guidebook on how to dress, declared that “A good pair of oxfords are the cornerstone of a stylish wardrobe.” 

But in the late 2000s, sweatshirted Zuckerberg clones ushered in an era of corporate casualization. In 2019, Goldman Sachs instituted a “firm-wide flexible dress code,” landing what many saw as a fatal blow to suit-and-tie formality. Surely, wealthy men still wear polished oxfords—65-year-old Jamie Dimon, the CEO of JPMorgan Chase & Co., seems unwilling to let his classic leathers go, routinely wearing them for his public appearances. But just as many monied men, seduced by the siren song of comfort, slip on rubber-soled mash-ups of sneakers and dress shoes from labels like Loro Piana, To Boot New York and Santoni. (These hybrids are not that dissimilar in concept from Cole-Haan’s well-known but oft-mocked LunarGrand collection, which debuted in the early 2010s. Those $150-ish shoes too-incongruously combined overly stiff leather uppers with sporty rubber soles often fabricated in off-putting yellows and reds.)

“I have a lot of brogues or lace-up shoes that I don’t gravitate towards anymore just because they might be too formal and are not always comfortable,” said Mark Esser, 34, who works in finance in Washington, D.C. While working from home during the pandemic, he shed much of his inhibiting work style and now, when it comes to footwear, primarily rotates through his pairs of lithe Open Walks. 

Why not just wear actual sneakers? Oh, many wealthy men do. At last July’s ”masters of the universe”-style meet-up, the annual Allen & Co. gathering in Sun Valley, Idaho, media and tech moguls like Barry Diller, Bill Gates and Flowcode CEO Tim Armstrong hoofed around between meetings in pedestrian New Balance, On and Nike sneakers.

But in certain fields, a sense of decorum, however eroded, endures. Barak Jacobov, 32, a New York real estate developer who still defaults to a suit and tie many days, said Open Walks are “dressy enough” to be worn with tailored slacks or a suit. He’s seen an uptick in colleagues wearing these Loro Piana not-quite sneakers and has found that certain colors of the shoes “can be a bit harder [to find] because they do tend to sell out pretty quickly.”

Andrew Weitz, the owner and founder of the Weitz Effect, a Los Angeles-based style consultancy working with high-net-worth customers, is a big hybrid-shoe backer (he even threw out the term “shneaker,” a coinage that was new to me). His clients are not “Selling Sunset” types looking to blow $1,200 on logoed Balenciaga sneakers or $2,000 Dior Air Jordans (though, now that sneakers are treated as an asset class, plenty of men with money to blow do hoard them). His clients are mostly not quite up on trends, men of some means who are happy to sink some cash into an easy-on-the-arches alternative to a dress shoe. Mr. Weitz steers them to rubber-soled leather shoes from both expensive brands (Santoni and To Boot New York) and relatively more economical ones (Scarosso and Aurélien, which makes a near dupe for the Loro Piana shoes at less than half the price). 

But it is the Open Walks and Summer Walks that have stoked a cult following. When you wear the shoes, “you’re in a club” in an if-you-know-you-know way, said Mr. Weitz, who favors “Loros” himself. These stripped-back shoes, much like, say, a solid black $595 Zegna cashmere ballcap, are yet another example of “investment normcore”—a wearable signifier that clues in other one-percenters that you, too, can splash out on something valuable that appears entirely banal to a less informed passerby. The shoes are a “subtle flex and I’m all about that these days,” said the mortgage banker Mr. Martin. Loro Piana’s shoes don’t scream like a pair of double G logoed Gucci sneakers, or beam like pearly Common Projects. They whisper, like a secret stock tip shared among friends.