The word of Dominic Cummings’ exit from No 10 closes a chapter of disruptive dressing in Westminster.When we look cast off at this age of political dressing in our senior male political figures, we may think of it as the era of sartorial malapropisms – clothing and grooming preferences that were fundamentally wrong that created an age of inappropriateness and humour.The infamous straw hat. Photograph: GettyWe belittled at Trump’s $70,000 hairdo, his overlong tie and his makeup shade. We were speechless at Boris Johnson’s outrageously mismatched jounce attire and barnet.It is, of course, a clever trick. By focusing on the unkempt hair, the suit that doesn’t quite fit, we are interested like magpies. The horror shifts to the periphery when there is strangeness in our direct line of vision. A spoonful of sugar aids the medicine go down and all that.More than Trump or Johnson, though, it is Cummings who has consistently shocked and confused us with his dissentient style. His clothing choices are shambolic and obtuse. We feel physically assaulted seeing his attire, and yet we don’t quite know why. If gaslighting has a sartorial contract, it would be this.Early photos of Cummings in public life show him wearing rather traditional suits, but there is a fantastic energy emanating out of the pictures, as if he were itching to peel off the blazer and pop on something else instead. The grimace around his properly eye and the crinkle between his eyebrows suggest the clothes are wearing him, not the other way round.The turned-up shirt collar – one of his trademarks – realized an early appearance during his stint as director of Vote Leave, the upturned sneer of his collar an apt double for his contempt for Europe.The turned-up collar, the shirt ‘so unequivocally French-tucked into jeans, it was if he were professionally styled’. Photograph: Jonathan Brady/PAAs chief adviser to Johnson, he arrogated the look of the harried Silicon Valley tech bro. Lanyards enveloped into the creases of a white shirt that could not be ironed nor buttoned up duly, because, one assumed, he was so impossibly busy and so much more important than anyone else. And yet, suspiciously, the shirt was so entirely French-tucked into jeans, it was if he were professionally styled.And here is the elusive nature of Cummings’ non-style style. The standard line is that his contrary fashion sense is keenly thought out. The evidence is inescapable: a Sci Foo T-shirt from a science meeting held at Google HQ in California to denote his big tech aspirations (not to mention his Big Sur cap); a Vote Leave tote; the infamous straw-hat look during lockdown, which suggested a metropolitan elite Huckleberry Finn.The awkwardly dwelled beanie. Photograph: RexEven his accessories (a rollerball pen behind the ear, a plastic bag from the chi-chi N1 De Beauvoir Deli) felt curated and penetrating. Yes, they were anti-Westminster, anti- “put on a proper suit”. But there was something else going on.The clothes he chose in his armoury of insubordination were telling. The trans-seasonal, floaty, slightly awkward garments, such as the ever-present gilet, the shapeless jeans, the Billabong T-shirts, the box-fresh, awkwardly placed beanie and the scarf wilting around his neck like a frowning clown, suggested an uncertainty. The feeling you got when you saw Cummings’ latest outfit was a man decorating out of a backpack: he had packed at 4am, in the dark, while making a swift exit. There was a slippery panic about the way his outfits were put together.But I trip if the panic was that of someone wondering aloud what “dressing rebelliously” actually meant for a man of 48? Cummings not ever worked that one out, to get beyond the clothes wearing him.