Leonardo DiCaprio in ‘The Wolf of Wall Street’
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“I want to dress like Bernard Madoff” is not a request that has warmed the ear of too many a tailor. However, it’s not as preposterous as it sounds when you consider the influence that Hollywood has had on Wall Street fashions for much of the past 30 years, often focusing on the financial district’s more shady dealings, as exemplified by the convicted fraudster.

In the film world, Wall Street has provided many a splendidly dressed financial rogue. There’s Jay Gatsby, the Long Island bootlegger brought to life on screen this year by Leonardo DiCaprio in Baz Luhrmann’s The Great Gatsby; Patrick Bateman, the psychopathic asset manager from Mary Harron’s film American Psycho (2000), based on the Bret Easton Ellis novel; and Gordon Gekko, the corporate raider played by Michael Douglas in Oliver Stone’s Wall Street (1987). The latest incarnation is Jordan Belfort, the real-life swindler played by DiCaprio in Martin Scorsese’s much-anticipated film The Wolf of Wall Street, opening this month in the US and elsewhere in the new year.

But really, who would want to dress like a hooker-slaying money man, or a Quaalude-quaffing fraudster? Most of us, apparently. “The dark side is always the more intriguing,” says Giorgio Armani, whose vintage 1990s suits are on view throughout the three-hour Wolf. “I think that the figure of the anti-hero on Wall Street, who is capable of making lots of money without showing any scruples at all, is extremely attractive to the public, whether they admit it or not.”

Smooth criminals are not a recent phenomenon. The likes of Al Capone, Pretty Boy Floyd and John Gotti, the “Dapper Don”, wouldn’t have dreamt of committing felonies in anything less than the finest tailoring. But dressing like a real-life crook doesn’t seem to have quite the same appeal as styling oneself as a fictional one.

Michael Douglas in ‘Wall Street’

Ellen Mirojnick, costume designer on Wall Street and its 2010 sequel Money Never Sleeps, says: “My vision for Gordon Gekko was to embody the glamour of old Hollywood and to be as sartorially splendid as the Duke of Windsor. Oliver Stone cornered me during filming, worried that none of his Wall Street friends dressed anything like this but I defended my creation and said it would become the reality. Sure enough, the LA Times called one day wanting to do an interview and the reporter told me every young man on the street was adopting Gekko’s style.”

Gekko represented a shift in formal menswear. What American Gigolo (1980) did for Armani’s flannel trousers, Wall Street did for the contrast collar, braces and unstructured suit: leisure was out and power was in. Josh Brown, a New York wealth manager and author of Backstage Wall Street, recalls Gekko’s influence. “Back then,” he says, “you always knew when a broker had just had a big commission because he would be in a new double-breasted Canali suit, Bruno Magli shoes and the two-tone blue dress shirt with the white collar. This would almost always be accompanied by a polka dot tie and suspenders à la Gekko. The Wall Street wardrobe from 1987 was still the guiding star for up-and-coming brokers well into the 1990s.”

In 2000, American Psycho’s Patrick Bateman (Christian Bale) took on the mantle of best-dressed sociopath, spawning a glut of “get the look” articles in men’s magazines. The character sanctioned an indulgence in the male self-image that the grooming industry has cashed in on since but, on the real Wall Street, the truth is often stranger than fiction, according to Brown.

Christian Bale in ‘American Psycho’

“Today things have gone the other way,” he says. “The traders almost never wear suits unless they have an event to attend. They dress exclusively in khaki pants or chinos and polo shirts with the logo of famous golf courses they’ve played. They are different from the client-facing guys. Their sartorial choices are more inspired by Steve Cohen’s SAC Capital – that’s why they’re all in dress shirts with a fleece vest [waistcoat] over them nine months of the year: Cohen kept the air conditioning pumping on his trading floor so the room was ice-cold because he thought it kept the traders awake. Guys from that firm began wearing fleece vests and then it spread to other hedge funds and trading firms. Now it’s basically a uniform.”

In Scorsese’s Wolf of Wall Street DiCaprio’s character is based on Jordan Belfort, who was convicted of crimes related to stock market manipulation and running a penny stock boiler room during the 1990s. In the film the protagonist sticks closely to the guiding principles of menswear in the late 1980s: flash, brash and with far too much cash.

“Belfort’s aesthetic was very nouveau riche, all money and little taste,” says the film’s costume designer Sandy Powell. “All these guys were suddenly very rich and were flying out Savile Row tailors to New York to be fitted but it was only really through their choice of ties that they could differentiate themselves or express their personalities.”

Josh Brown’s first Wall Street-related job was as a summer intern cold-calling at Duke & Company, which was started by Belfort. “It was the summer of 1996 and there were 200 ‘senior brokers’, many of whom were nightclub bouncers and bartenders just a few months earlier,” he says. “For most of the guys in the brokerage business in the 1990s they never had any exposure to actual businessmen, so the only way they knew what they were supposed to be wearing was from the movies. One broker had five different-coloured Porsche 911s so he could co-ordinate them with his ties.”

Given the faultlines in today’s financial markets, such sartorial flamboyance has given way to a return to classic tailoring. Thom Whiddett, one half of London tailors Thom Sweeney, says: “It’s very difficult to teach or buy style but when I’m advising City clients on how to dress powerfully it always comes down to keeping things simple. Focusing on the cut of the suit and its silhouette is much more important than extraneous accoutrements.”

Take, for example, the Balenciaga collection for spring/summer 2014. Its dark and streamlined silhouette says power in an understated way.

For wolves wanting to break from the pack, Lanvin offers an unstructured double-breasted jacket – paired with silky jogging pant trousers on the catwalk – a look that would no doubt raise eyebrows in the boardroom. Indeed, the double-breasted jacket was far more visible this season than previously, most notably at Ermenegildo Zegna, where separates reigned over two-piece suits. Does this mark the beginning of a return to a more relaxed shape of power player? That remains to be seen.










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