They’re not the sort of clothes you wear to meet your boss – unless your boss is Boris Johnson. You almost have to applaud the PM’s adviser’s messy aplomb

Boris Johnson’s victory last week meant the ascension of not only the Tories but also his “wild man of Westminster” look. With his unkempt and just-fell-out-of-bed-into-some-clothes-at-4am vibe, Johnson was once famously seen in Hawaiian running shorts with a skull logo beanie (and not as part of a sponsored charity run). His sartorial heir apparent is Dominic Cummings: a fan of gilets and totes. On Monday, Cummings reached Johnson-like levels of zany with the outfit he wore to Downing Street: a £195 khaki-green Finisterre Nebulas puffer jacket over a V-neck green jumper worn with a striped Royal Speyside cashmere scarf and a grey woolly hat.

It was the details of his outfit that were gripping: shirt untucked and spilling out of his trousers, the rim of his beanie flipped in an awkward zigzag formation and the scarf resting limply on his shoulders. It screamed “Vitamin D deficient”, “Tech bro adjacent” and “Oh, it was wash day, so …” They’re not the sort of clothes you wear to meet your boss, unless of course your boss is Boris Johnson. Cummings’s look recalls a return of the “sleb-rity”, the male celebrity who dressed like a slob.

It was big in 2018, and Esquire called it “the summer of sleaze”. The magazine associated it with celebrities such as Justin Bieber (who dressed like Jeff Spicoli, Sean Penn’s stoner character in Fast Times at Ridgemont High – see also Pete Davidson and Jonah Hill), Shia LaBeouf (Uggs, denim cut-off shorts) and Post Malone (dresses a bit like a wrestler on his days off). The style was a very Los Angeles convergence of skater looks and stoner aesthetics.

On a political level, Cummings’s look falls in the lineage of Donald Trump, who helped weaponise the Political Bad Fashion Choice. In an era where a meme becomes a shareable talking point, Trump’s combovers, wrong-coloured foundation and too-long ties were catnip for both conservatives and liberals, who wrongly assumed that mockery would lead to diminishing levels of popularity.

Facebook Twitter Pinterest Cummings’ look in full. Photograph: Rick Findler/PA

For Cummings and Johnson, the manipulation of the buffoon archetype has paid electoral dividends. As Vanessa Friedman has noted, “as a longtime fan of PG Wodehouse and Chaucer, and a student of history, Mr Johnson surely understands the way bumbling plays in both the public mind and the British character narrative”.

It is as if the thinking goes something like: “He’s lovable and not a real threat because he wears a crazy beanie or looks like an orange,” all the while inflicting policies on the country that affect the most vulnerable members of society.

As white, male, privileged men, they can get away with dressing like slobs and unlike, say, a black teenager in a hoodie, they not only get off consequence-free but become a “lovable rogue” figure.