MMuch has been made this week about how short Rishi Sunak’s pants are, with some commentators calling the mid-ankle crop “baffling” and a political liability. So much has been read into something as insignificant as the point where his otherwise bland trouser leg meets his bland sock speaks volumes about the state of British politicians’ dress.
In the forefront of which: the British Prime Ministers. While not known for being interestingly dressed – much less for being well-dressed – there were a few who stuck their heads above the parapet to display bland suits and boring black shoes. to show some flair. When they have done so, they have been seized – either to provide proof of their authenticity, to cement their popularity at the polls, or to be weaponized and used to prove they are elusive, out of touch or unfit for functions.
From homburg hats to leopard-print kitten heels, these prime ministers have given commentators a little more to talk about.

August Henry Fitzroy
He entered Parliament via a pocket borough, served as Prime Minister for only one year and 106 days between 1768 and 1770, and was early described as “a young nobleman already ruined by gambling”. The third Duke of Grafton was portrayed as a “macaroni”, the precursor to the Georgian era of the fashion-conscious dandy. But, as fashion historian Valerie Steele points out, while there is evidence that he was a “gambler, a cuckold, an adulterer and a corrupt and unpopular minister”, it’s unclear whether he actually wore a macaroni dress. This did not prevent the cartoonists from arming a contemporary style of dress to criticize a Prime Minister considered sleazy and lacking in discretion.
Anthony Eden
A fashion icon in that he was apparently known simply as “Eden” on Savile Row, the prime minister from 1955 to 1957 was known for his single-breasted waistcoats, lounge suits and homburg hat. His legacy cannot be unraveled from the Suez fiasco but, less known, is that he was an unexpected pioneer in nail polish. As newspaper columnist AN Wilson commented, he was “by far the handsomest person, of either sex, to hold that office in the 20th century” as well as “the only British Prime Minister known to paint his fingernails”.

Benjamin Disraeli
Prime Minister briefly in 1868, then between 1874 and 1880, Disraeli played a role in the creation of the modern Conservative Party, but his sartorial heritage is largely absent from his descendants. Not afraid to dress up, a guest at a dinner one day noticed her outfit consisting of a velvet coat, purple trousers with a gold band, a scarlet waistcoat, “long lace flounces falling down to her fingertips, from white gloves to several of the shiny rings on the outside and long black curls waving over her shoulders”. If only more prime ministers would take such sartorial risks.

Harold Wilson
Known for his raincoat and Gannex pipe, the former Labor Prime Minister’s sartorial legacy (1964 to 1970 and 1974 to 1976) is so powerful it seemingly reached the decades to inspire Harry Styles. When things were going well, his style was seen as reassuring and trustworthy. But when things went wrong, his detractors portrayed his pipe smoke as obscuring and his raincoat as evidence of his poor judgment. In a 1976 speech, Margaret Thatcher zinged with Wilson’s raincoat, saying he “didn’t protect the country.” Joseph Kagan, the businessman who invented the waterproof fabric from which these coats were made, was knighted and then peered by Wilson. However, after a conviction for theft for which he went to prison, he was stripped of the knighthood.

Tony Blair
As cultural commentator Peter York once wrote, “Tony Blair dresses like the successful businessmen of his generation dress. Paul Smith costumes, like guitar playing, form a bond with these peers. Blair’s suits were plain, but polished, and his style was informal and felt modern in the same way that New Labor felt modern. The devil was in the details – from the hidden illustrations of naked women in the cuffs of his shirt to the suit jacket slung sluggishly over the shoulder, a signal that he had jokes as well as the budget.

Therese May
From her strong, stable collars to her shiny suits and leopard-print kitten heels, May may have been robotic and greige in her delivery, but she was, compared to your average Westminster body, experimental in her choices of wardrobe. If she wasn’t dressed well, she was certainly dressed interestingly – from the twofer (a coat, designed to look like two) she wore on budget day to the gold leather pants she wore for a photo shoot. from the Sunday Times. The edgiest of all was the ball gown she wore to vote in Boris Johnson’s vote of no confidence.