Whatever Happened to Well-Dressed Villains?

Among a particular cohort online today, there’s a sense that the disappointing present can’t hold a candle to the glories of the recent past. “We used to be a proper country,” they’ll meme with varying levels of sincerity, sharing images of a 1990s Pizza Hut salad bar or the well-stocked shelves of a Blockbuster Video.

Those pining after an America that existed before Covid, Trump, and possibly their own arrival on earth may add one more complaint to the list: a total dearth of well-dressed villains. Whereas greed was personified for an earlier generation by the razor-sharp tailoring Michael Douglas wore as Gordon Gekko in Wall Street, today brings us the dumpy dorm room aesthetic of Sam Bankman-Fried, the confounding crewneck-under-a blazer look favored by George Santos and the baggy, rumpled suits of our most recent ex-president.

An instant rejoinder to this critique is that Gordon Gekko was not a real person (although he was purportedly based, in part, on an actual convicted insider trader). But we need only to look to the early aughts to find Bernie Madoff, a Ponzi schemer who dressed like an Upper East Side aristocrat in resort baseball caps and quilted jackets and owned close to 300 pairs of cult-favorite Belgian Shoes. Or back to the '90s, when Christian Karl Gerhartsreiter conned his way up Boston society disguised as “Clark Rockefeller” in Brooks Brothers and J. Press.

Seeking answers as to why contemporary villainy has proven so sartorially underwhelming, I reached out to the man responsible for Gekko’s power suits: Alan Flusser. Flusser, who in addition to his wardrobe work on Wall Street penned the evergreen style tome Dressing the Man, sees the sad state of bad-guy dress as a reflection of society’s present mores.

“I think the villains of today dress at a taste level that’s more a function of the taste level you find in the culture,” he says.

It’s a funhouse-mirror inversion of the “greed is good” ‘80s, when Gekko—as unsubtle a cinematic heel as they come—was heralded as a sartorial anti-hero. Flusser recalls lecturing at business schools post-Wall Street and realizing that budding financiers wanted to be Gekko, right down to his gut-end braces and double forward pleats.

“Guys were willing to put away his less savory characteristics to want to become a Gordon Gekko, someone who had that kind of lifestyle. Gekko symbolized that, not only by the way he behaved and operated, but the look that the clothes gave him.”

Indeed, Flusser says the film’s 1987 release set off a boomlet for tailored clothing, with wannabee Gekkos visiting his eponymous custom clothing shop and natty New York retailers in search of pinstripes and contrast collars. And as recently as the 2010s, one might find Wall Street playing on screens in high-end department stores across South America and Japan.

While Gekko’s fate is sealed in the film by a wire recording, the look he embodied was brought down by more banal means: casual Fridays. What began in the 1990s as a gradual loosening of office dress codes accelerated to their near-total abandonment by the 2010s, with the experience of Covid-19 giving the suit-and-tie ensemble its apparent coup de grâce.

As a result, men are increasingly at sea when it comes to wearing anything other than casual clothing. “There are a lot of men who want to dress up. They just don’t know what that means anymore,” Flusser says.

Cue Santos and his penchant for wearing clingy crewneck sweaters under orphaned suit jackets with low-rise chinos and white-soled dress sneakers (some of which may have been purchased with campaign contributions, as alleged in a 13-count indictment from federal prosecutors). It’s a mess of mixed signals that suggests someone flailing to fill a role.

While it seems clear that Santos is attempting. and failing, to look like an honest legislator, SBF’s pre-disgrace uniform of shapeless tees, shorts and New Balances with athletic socks may have been a conscious camouflage. Was this LAN party get-up an authentic expression of his style agnosticism, or a calculated ploy meant to suggest a genius—and trustworthy—tech wiz?

Flusser leaves it at Occam’s razor, chiming that SBF “clearly has no interest in clothes whatsoever.” But he does see a Gekko-esque property in the casual threads preferred by today’s tech moguls, which may serve as counterintuitive status signals.

“Michael Douglas wanted clothes that outclassed everybody… Mark Zuckerberg can effect in today’s world the same kind of power by surrounding himself with guys in shirts and ties yet walk into a meeting dressed in jeans and a t-shirt,” he says.

Lost in the middle is the average guy, who might feel out of place wearing a suit but doesn’t have the billions required to turn a hoodie into a power play. Such men now constitute the client base of Alan Flusser Custom, which was taken over by its longtime director Jonathan Sigmon after Flusser retired from the business in 2020.

“Day to day our clients are certainly more casual than in years past,” Sigmon says of the current climate. “About half of the folks I see in the shop are wearing a suit or sport jacket on a daily basis, and it's even less than that during the summer.”

What’s replaced that tailoring is often a polo shirt paired to chinos or dress trousers. To elevate this modern uniform, Sigmon prescribes a softly tailored sport jacket in a texture-rich fabric, perhaps with a houndstooth or glen plaid pattern if a client is feeling adventurous.

“Paired with chinos or jeans, it's a simple way to look more elegant, and the architecture of a well-designed jacket is more flattering than a simple vest or pullover,” he continues.

And for those that refuse to get anywhere near a lapel, Sigmon settles for getting the basics right. “In that case we focus on great shirts that fit well with collars that frame the face in a flattering way. A proper collared shirt and a well-cut pair of pants still go a long way towards looking stylish and put together.”

While reflecting on the clothes in Wall Street,Flusser brings up another American institution: the mafia. He cites “slickly dressed” criminals as being the progenitors of the power suit, which rode its way up the respectability ladder to the top of the New York financial world before it came tumbling back down.

Now that our wolves never stray from sheep’s clothing, Flusser fears that the Gekko look could be headed for extinction. “I think those subtleties are going to be left without anybody to pick them up,” he says.

On the contrary, now might be just the right time to start trusting a man in a well-cut suit—or at least give that sport jacket hanging in the back of your closet a second chance.

Editor's note: Santos and Bankman-Fried have both pleaded not guilty to the charges against them.

You Might Also Like

• Kid Cudi Is All Right

• 16 Best Shoe Organizers For Storing and Displaying Your Kicks