Dominic Cummings has put the blowtorch to Whitehall. From orchestrating a Brexit campaign of half-truths to pushing for an unlawful prorogation of parliament (which, by the way, hasn’t been enforced in such a manner since 1948), the Prime Minister’s right-hand welder is a sound tradesman when it comes to dismantling the scaffolds of Westminster. To those who pride due process however, Cummings is seen more as a cowboy builder.

Everything breaks from convention. He’s no Conservative Party member, but continues to reform the Conservative Party in his own image. He moved from a short-lived career in commercial aviation to political strategy. And Cummings doesn’t look like the typical special advisor either. One can assume he’s too busy delivering Brexit to keep up appearances, the dry cleaners usually closed after a long, hard day of shrugging off death threats to MPs.

Cummings returns to Downing Street earlier this month Tolga Akmen

Or so it would seem. Boris Johnson, the patron saint of twee Etonian oafishness, has arguably spent decades cultivating this persona. A Manhattan-born Balliol grad is probably aware that decorum doesn't hang on a zipwire above Victoria Park. A climb of the ladder to Downing Street isn't without some serious media consultancy, either. And, as the chief architect of Boris 3.0 - the current bullish head boy incarnation - Cummings leaves nothing to chance in the public eye. That includes his own uniform.

Hollie Adams

Think of it this way: a senior special adviser to a cabinet position is serious work. And so ‘serious’ clothing is de rigueur for hired politicos on salaries north of £70,000. Less blue skies tech CEO, more blue blood IBM board member. That means a proper suit within the grey-navy-black trifecta, tie tied correctly, smart but forgettable shoes, and ideally not a hint of personality in sight. Such things are for the elective representative you work for and the newspapers they dodge questions from. Of course, this uniform isn’t at all sharp. But that’s the point. Special advisors (referred to as ‘spads’ by Whitehall insiders) are built to blend in, and thus well below the parapet when scandal inevitably ensues.

Cummings subverts this. There’s no semblance of smartness. Instead, we see tucked in shirts exchanged for unbuttoned, unwieldy shapes. Rather than a suit, there’s a gilet of some form, flanked by baggy Barbour jackets, detachable fleece linings and the arch-enemy of conservative dress codes around the world: jeans. As Sky’s Adam Bolton rightly observed, such gear is inappropriate for one of the highest offices in the land.

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I disagree. There are dress conventions and Cummings is deliberately defying them to show his contempt. That is not appropriate from a senior representative of the Prime Minister. https://t.co/NffTbIofue — Adam Boulton (@adamboultonSKY) September 27, 2019

Of course, such criticism isn’t solely reserved for the right wing. Upon his ascendance to Leader of the Opposition, Jeremy Corbyn was pilloried by the press for looking un-ministerial, clad in ill-fitting mismatched tailoring and, like Cummings, sans tie. Even David Cameron famously told the avowed socialist to “put on a proper suit” during a notably heated exchange in 2016. But come the snap election of the following year, Corbyn smartened up. Suits matched. Ties were tied properly (in a brilliant shade of red, naturally). And, despite crawling approval numbers and a small army of detractors, Corbyn at least dresses, occasionally, for the job he wants. 2017's 'ties optional' ruling in the House of Commons may have loosened the dress code, but expectations still stand.

Cummings attends the annual Conservative Party Conference, Manchester Jeff J. Mitchell

Cummings refuses to follow. Instead of mimicking colleagues at the top of their game (both Cameron and Tony Blair’s right-hand men abided the grand tradition of deskside uniformity), the current Downing Street showrunner is remoulding the office code. Perhaps that’s because Cummings is unlike any of his predecessors. Reputation precedes him. Indeed, few other senior aides have ever commanded such a public profile: Jonathan Powell, Edward Llewelyn and Gavin Barwell - the names of the last three chiefs of staff - are not of the household. By very token of Cummings’ newfound notoriety, he boasts the unique concession of being able to stand out, to break the rules - and it’s this bonfire of deregulation that led to his notoriety in the first place.

Just this morning, Alistair Campbell told radio station LBC that “Dominic Cummings goes out of his way to attract attention”, whether that’s through an unlawful dissolution of parliament, public spats with MPs, or, indeed, via an out-of-place uniform that intentionally flouts the most hallowed of dress codes. Even at the well-snapped spectacle that is the annual Tory Conference (perhaps the most important optical event of the year for a political party), there was a further casual doubling-down in the guise of an ill-fitting hoody. The smarter the function, the laxer it gets.

Tolga Akmen

In his personal blog, an ominous foretelling of how British politics was to be redrawn, Cummings shows contempt for the system. He speaks of "breaking the wheel" of the civil service, instead encouraging a reliance upon big data over officials that refuse to "learn from evidence". Following a "coming collapse and reshaping of the British parties", the 47-year-old sees his Silicon Valley gospel as paving a new form of governance, on quick-thinking capabilities and the removal of bureaucracy. His way, in other words. And, like tech leviathans Zuckerberg and Musk, Cummings lays waste to the old office, including the suits that fill them.

“We’re enjoying this,” Cummings was quoted by The Times as saying of the current circus. He wants to provoke parliament, after all. He really wants to provoke the system. Like his entire strategy within Downing Street, the clothes too can be seen as a deliberate measure to inflame. To communicate a message. And, though Home County gilets may seem an innocuous cloak for a man on the fringe, know that they’re another pair of defiant middle fingers to an establishment he so clearly loathes.

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