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This guy could probably take your retirement savings, if he wanted.
Photo: Petar Chernaev

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Clothes Make the Con Man

Why a well-cut suit or an elegant gown is a swindler’s best friend.

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The Los Angeles Times’s much-hyped and deeply salacious podcast Dirty John explores a “sweetheart scandal” that turns exceptionally sour. When it came to John, a California con artist who targets the trusting, thrice-divorced Debra, there were a lot of red flags. He was entitled and aggressive from the first date, refusing at one point to leave his prospective victim’s apartment. His personal history was muddy and vague, and he had questionable associates. And his reported occupation of “freelance anesthesiologist” is probably not a thing.

But the real first alarm bell for his mark’s family was John’s clothes. The man who claimed to be a doctor donned worn-out sweats and other ill-fitting attire, along with hospital scrubs that seemed more costume than uniform. One of Debra’s daughters recalls seeing him for the first time: “I looked at him head to toe and thought, oh, this loser.”

But consider Dirty John and his suspect scrubs the exception that proves the rule in the world of the con. The most iconic con artists —from ne’er-do-well tenants to fake aristocrats — typically choose their attire with careful attention. In salacious stories of fraud, victims often raise a con artist’s fashion or style choices as a key part of how they formed sufficient trust to give away large sums of cash, keys to their apartments, and even love.

But con artists, for all of their questionable conduct, don’t just enjoy luxurious fabrics or don a costume for kicks. They’re taking advantage of the superficial, often split-second judgments that each of us utilize to evaluate the strangers that surround us. And we are remarkably vulnerable to appearances — even though logic might tell us that they’re very simple to manipulate. Taking a look at con artists and their styling choices helps explain just how much we depend on external physical cues like fashion as a sorting mechanism.

Consider the case of Cassie Chadwick. In Maria Konnikova’s podcast about con artists, The Grift, she explores Chadwick’s case, rooted in the social flux of the late 19th century, in an episode called “The Self-Made Heiress.” “For as long as we’ve had aristocrats, we’ve had people pretending to be aristocrats,” notes Konnikova, author of The Confidence Game: Why We Fall for It… Every Time. Chadwick starts out passing bad checks in a small town to buy pretty things, but she graduates to impersonating a Carnegie, operating a Ponzi scheme in which she targeted men spellbound by her charms.

Konnikova describes how Chadwick’s preferred gown — worn anywhere she was hoping to be noticed — was perfectly crafted to match her fictitious backstory: “an elaborately embroidered form-fitting top, sleeves modestly covering her arms, a swooping floor-length skirt pleated with a pronounced train — one made for riding in carriages, not walking on sidewalks. The kind of dress that screams of servants to lace and unlace.”

Victims of con artists report, over and over, their disbelief at being ripped off by a guy who “looked just like a lawyer.” Christian Gerhartsreiter, who famously lied about being a Rockefeller heir named Clark, had the wardrobe of an occasionally employed middle-aged trust funder down. When he was arrested in 2008 for kidnapping and murder (not to mention fraud), he was wearing khakis, a Lacoste polo shirt, and brown boat shoes — like he was only on land when briefly between yachts. In a pre-Rockefeller incarnation known as Christopher Crowe, one observer noted about Gerhartsreiter “every article of clothing, from his slippers to pajamas, was monogrammed.”

Konnikova says that you would be hard pressed to find a con artist who doesn’t use fashion and style as key tools. “Those things help you create an immediate impression in the first seconds of meeting someone that are crucial to success of the con in the long term,” she explains. In her book, she writes about the first use of the phrase “con artist” (short for “confidence artist”) during the trial in New York City of William Thompson in 1849.

“Thompson dressed to the nines, with a three-piece suit and watch fob,” says Konnikova. He would stop equally dapper gentlemen in the street, pretend they were already acquainted, and then ask if they “have the confidence to lend me your watch until tomorrow?” Konnikova notes the quixotic and brilliant formation of the question. “He’s not just asking if you’ll give him your watch,” she says. “He’s asking if he’s the kind of person you want to trust, if this gentlemen’s code still holds.” Thompson’s con centered on his approach of a similar social class as signaled by his clothes. And by the time he was caught, his apartment was overflowing with watches.

Robin Ennis, a realtor who deals in high-end properties in Toronto, had her own run-in with a modern-day Thompson who managed to con his way into an expensive property and then refuse to pay rent. The longtime fraudster showed up in her office in a tony neighborhood and spoke of elite connections and his grandiose art collections. He looked the part. “He first came into my office in tennis whites after playing at a private club, he was dropping the names of senators, and he just looked so prominent,” says Ennis. “He seemed like the exact type of man, with the mustache and silver hair, who belonged in those places. But he steals fancy clothing like navy blazers and expensive leather goods, and everything about him is fake.”

The careful dressing behind these cons often take advantage of a psychological phenomenon known as “affinity bias,” where we have intuitive trust and fondness for people who appear to be like us. And we often judge relative affinity in an instant. So-called “thin-slice judgments” — where we make snap decisions about people often based on limited information — can depend heavily on personal styling. “You always want to dress like the social milieu you’re trying to infiltrate,” says Konnikova. “There’s so much research that shows that you trust people more if you think they’re similar to you — and one of the biggest cues is clothing.”

But bias goes beyond affinity. Research also suggests that we’re persuaded by signs of elevated status and conventional success — as transmitted through our clothing. One study found that — after a three-second exposure — participants showed a preference for men wearing more expensive suits, identifying them as more confident and successful. “When we lack information about someone, know nothing about them, all we have to go on is visual appearance,” says Karen Pine, author of Mind What You Wear: The Psychology of Fashion. “So we make snap judgments but we don’t always get them right.”

Even if we’re not actively grifting, many of us have our own experience with trying to dress for a different role. When I received a small windfall several years ago, the first thing I did was buy an insanely expensive and completely spectacular Burberry coat. People’s eyes would widen as they drank it in, often extending a hand to touch the buttery sleeves. There was something about that coat — really, just a confluence of soft houndstooth wool and smooth black leather — that made me feel so powerful that it was almost like adopting an alter ego every time I slipped it on. I swear wearing that coat earned me deeper respect from acquaintances, colleagues, and sales clerks in high-end department stores (where I couldn’t actually afford to buy anything because I had spent all of my money on the coat).

Maybe the coat, which outclassed me by several degrees, did indeed impress people, or perhaps they were just picking up what I was putting down. Studies have shown that what we wear affects not just how we’re perceived but how we actually feel. The term “enclothed cognition” is used to describe the influence that clothes have on the wearer’s psychological processes. For example, when wearing a lab coat associated with a doctor, some research has found that the wearer is more attentive and conscientious when given a task. So it’s entirely possible that con artists dress the part not only to influence others but also to bolster their own sense of legitimacy — that wearing the three-piece suits of a trial lawyer or the polo shirts of the leisure class can actually help a con artist embody whatever role he or she is playing.

In a recent opinion piece for Business of Fashion, Luca Solca, head of luxury goods at BNP Exane Paribas, suggests that the luxury is driven not by long-wealthy but by the upwardly mobile “new money” rich who want to look the part: “How better to define their new identity than by possessing things other people don’t have. Ultimately, it’s a case of ‘I have, therefore I am’… They go through a period of over-consumption to soothe their insecurities and demonstrate their worth to their global peers.”

But it’s worth asking why we’re still so convinced by an expensive wardrobe in an age when almost anyone can charge a convincing $2,000 outfit or a coveted purse to a credit card. My fancy coat really only said one true thing about me: that I own an expensive coat. But it always seemed to communicate so much more. “We might like to think that what we wear doesn’t matter, but it’s part of the package,” says Konnikova. “Unless you make a very conscious effort, you can’t override it. People don’t even realize they’re doing it.”

Con artists know — instinctively or otherwise — that these things matter. And their fraudulent identity often falls away when they’re stripped of those sartorial tools. Ennis, the realtor in Toronto, says she recently saw her con artist in court, where his appearance was considerably shabbier. He looked like a completely different person than the one she met that afternoon in her office. “He didn’t have his elegant navy blazers and crisp white-collar shirts,” she says. “The little prince has been stripped of his fine clothing.”

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