Sam Bankman-Fried and the power of dressing badly

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One of the horrifying things we have recently learnt about Sam Bankman-Fried, founder of the crypto exchange/fraud/morality tale FTX, is that his clothes were not a power play. Running a multibillion-dollar business while wearing a T-shirt, rumpled shorts and beaten-up trainers appeared to be bog-standard techno-peacocking. I can dress like a failure-to-launch video-game addict because it’s all about meritocracy here at FTX, we’re too busy disrupting to care about clothes, and besides I’m richer than you.

How unpleasant to discern that Bankman-Fried actually was a failure-to-launch video-game addict, just one who somehow got hold of a lot of other people’s money. That is one possible interpretation, at least. A less charitable suspicion is that Bankman-Fried was a pure criminal all along and his clothes were part of the grift, a contrivance designed to project idealism, single-mindedness and creativity. I leave it to readers to decide which interpretation they prefer. The question that concerns me is the power of dressing badly, and how it can be harnessed.

The obvious example, as tired of it as we are, is former president Donald Trump. I used to wonder why he preferred his suits several sizes too large. I was being stupid: he wears them that way to conceal that he is very fat, and it sort of works. The shiny, overlong ties help the tenty suits look more proportional and, again, distract from the gut they rest on.

Donald Trump in large suit jacket and long tie in 2019 © AFP via Getty Images

It is easy to laugh at all this, and I do. But one must acknowledge that Trump’s poor clothes, whatever his reasons for choosing them, are a fantastic success. They fit perfectly with what he is trying to project. They are evidently expensive, attention-grabbing, brazen — and he was elected president in large part for embodying wealth, drama and a refusal to apologise.

This is Rule No 1 of dressing badly for success: looking attractive matters a lot less, for political or professional purposes, than telling your story.

There is another great example from the other side of the aisle. I have written about John Fetterman, recently elected senator from Pennsylvania, before. In his former job as lieutenant-governor, he rocked workwear. He wore a Dickies work shirt in his official portrait and looked great. But when he showed up to work at the Senate, he was wearing a suit — a very, very badly fitting, cheap-looking one.

It’s hard to find an off-the-rack suit when you are 6ft 8in, but more to the point, the suit was both on-message and professionally appropriate. I’m representing working-class people from a working-class state, his get-up said. There is a reason that the awkward opening between a cheap suit’s lapel and the shirt collar is known as the “prole gap”.

At the same time, though, Fetterman was bowing to the rules of the institution. He was wearing the uniform required for doing the work of the nation. Rule No 1 observed, and Rule No 2 demonstrated: when dressing badly for effect, it is especially important to show respect.

Rule No 2 was why Boris Johnson, who took ostentatious pleasure in his dishevelled clothes, was not ultimately a successful bad dresser. He did not respect his audience, did not back up his indifference to clothes with commitment to more substantial things. If you refuse, on principle, to show that you care through clothes, you have to find another way to show it. Boris never quite could.

A man strides through a corridor with other men in suits following behind him
US senator-elect John Fetterman swaps his Dickies work shirt for a suit for his arrival at the US Capitol in November © AFP via Getty Images

The longtime Massachusetts representative Barney Frank, America’s dishevelled political dresser par excellence, ran ads during one re-election campaign in the 1970s with the tagline “Neatness isn’t everything”. What was effective about the campaign was that, by all accounts, Frank was both a serious political intellect (see Rule No 2) and natural-born slob. This is Rule No 3 of power bad dressing: it can’t be completely faked. Bad clothes fail as a power move if you don’t feel at least somewhat at home in bad clothes.

I always thought that in another job Mark Zuckerberg might have been very happy in a suit. There has always been something unconvincing about that hoodie, and this is part of Zuck’s chronic unpopularity.

Clothes are always a costume, a mask. And there is no costume more traditional or more stagy, for people in power, than the costume of indifference. That we are all familiar with this posture makes it harder to pull off. Hence the three rules: tell a good story, show that you care, and mean it, just a little.

Robert Armstrong is the FT’s US financial commentator

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