City Boy Style Rocks


It’s happened again. Rogue trading has hit the headlines. Only this time, instead of sultry Singapore, patrician Paris is the financial crime scene and there is something curiously apropos about that. Just when people had started, once more, to write off city boys as boring, avaricious creeps, up pops one of the bad-boy ‘rock stars’ in one of the world’s most stylish capitals having bled his employing investment bank SocGen of a whopping $7 billion. Forget high-stakes poker, forget trashing hotel rooms and mind-bending narcotic experimentation. Taking thousands of millions, squandering them and then elegantly covering the trail is the way to rock and roll and it has put the city boys back in the spotlight.

With a nervy start to the financial year, people were already beginning to turn their lenses on the unassuming bean-counters in the towers of glass and steel but this news has really set the pulses going. No one romanticises or fantasises about the striped-shirt brigade who spend their days with screens and phones; they are the antithesis of romantic figures, merely slaves to King Midas who occasionally flash their inner vulgarity with ostentatious consumption and tasteless over-tipping. Their working lives are chronicled anonymously in the salmon-print of the Financial Times consistently referred to in herd-like terms, avoiding reference to any individuality, and we are led to believe they are merely miserable souls whose Damoclean mistake was to follow the road to riches rather than honest worth.

A lot of this is, of course, drivel. Yes, these chaps are driven by money, but find me one Hollywood egotist willing to accept the minimum wage for their work. They aren’t exactly long-haired poets or suffering artists of great talent, but they take huge risks and not merely to double-line their own pockets. They also work, for better or worse, pretty damn hard to make money and they are necessary in this zero-sum world. Lastly, their salaries, often criticised for being simply too large by point-scoring neo-liberal politicians, are in fact proportionate to their performances and are taxed like every other sum of legitimate money.

One other thing, which is likely to be scoffed at, is an observation of mine that in fact, a lot of city boys have the style nous that other professionals lack. The lawyer is smart, but lacking in chutzpah. The doctor is generally over-casual and unremarkable. The city boy is a Wall Street tiger: he has stripes and he will bally well show them.

However, the hard, mathematical types who hoard pictures of their families on their desk, next to their novelty chess-boards, resent this city boy tag, so I isolate them from my spoons of praise. They are the dry, tee totalling mail-order catalogue side of the city to whom style is about as important as moon exploration to a budgerigar. The true city boy sweeps in wearing pinstripes leaning towards the muted sartorial classicism of Jermyn Street in contrast to the advertising titan in Soho, clothed in Duchamp and Richard James. He wears shirts and ties with ease and pride, and even bothers to seek advice in Thomas Pink from the style consultants for counsel on combinations. At his side swings a magnificent Malacca umbrella from James Smith.

Though dressing down has been the recent form for vast swathes of city folk, the indication is that some of the British are standing firm. A stockbroking friend of mine is a strong believer in the city uniform and refers to the attire of the relaxed New Yorkers, quite abruptly as ‘that casual crap’. Whereas casual financial-scientists from Wall Street see themselves as belonging to the distinctly un-yuppy Pixar generation, the stalwarts of the Square Mile stand proud with the dignified and unapologetic air of George W. Banks. The markets can go where they like; sartorial stoicism is to be saluted.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at


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