Best dressed politicians throughout history

27 November 2015

Best dressed politicians throughout history

Few careers require getting it sartorially spot-on quite as much as a politicians. In a world of intense media scrutiny, they have to convey a sense of reliability, self-assurance and morally inscrutability.

A fashion faux pas might quickly be represented as some kind of psychological defect. Wearing a garishly-coloured tie could have a politician portrayed as an eccentric maverick. An unbuttoned shirt collar might provide clear evidence that they’re wilfully slapdash.

But given the limited room for manoeuvre, there are those that have managed to stay within the acceptable boundaries of political protocol while still looking that bit classier than the rest.

Here are 5 individuals who have breathed a sense of style into politics and made it seem ever so slightly cooler. 

Winston Churchill


The same man that inspired a nation through the Blitz and helped restore peace to war-torn Europe also wore silk pyjamas to bed. Yep, Winston Churchill was a pretty stylish guy.

Churchill’s most iconic look was arguably his tailored three-piece suit, complete with bowtie, pocket square and Homburg hat. Many of his outfits were designed by Henry Poole & Co (one of the most distinguished tailors on Savile Row), but Churchill was also known for his far less formal ‘siren suit’.

This all-in-one zip-up could be hurriedly slipped into when he was scrambling to his bomb shelter during a raid. The great man had a number of these made, including an extravagant red velvet number that featured its own cigar pocket. Now that’s classy!


Barack Obama


No question, Obama has brought a serious sense of style to the White House. But he actually keeps his suiting simple and consistent.

The U.S. President has gone on record as saying he tries to minimise his decision-making time, so only gives himself the choice of a charcoal grey or navy blue suit to keep things straightforward.

Obama looks equally good sporting the smart casual look. Mirrored shades, baseball caps, button-down shirts with smart denim jeans…where other politicians attempts to appear ‘one with the people’ seem contrived, Obama pulls it off with casual ease. 


Nelson Mandela


Nelson Mandela was well-accustomed to wearing a sharp suit. In the early years of his career, he proudly wore a wide lapel suit with folded pocket squares - every inch the image-conscious young leader.

But after his time in prison, Mandela wanted a new style and decided to swap the rigid formalities of a conventional suit for a range of elegant, tailor-made silk shirts. Impeccably pressed and emblazoned with lavishly coloured African patterns, they became the great man’s most distinctive style of dress.

Ultimately, Mandela’s expressive way of dressing was an extension of his own natural warmth and charismatic personality, reaffirming him as a true individual.


Nicolas Sarkozy

The former French President might have been a controversial figure while in office, but he undoubtedly cut a dashing figure. The epitome of French style and sophistication, Sarkozy made it onto Vanity Fair's annual list of best-dressed people in the world in 2007.

He was also known to love his designer brands. For his inauguration, Sarkozy opted for a stylish Prada suit, and he was also a fan of Dior. Once known as “President Bling Bling”, the Frenchman’s singer and former model wife, Carla, had him ditch his once brash outfits and jewellery for a more conservative approach.

Darker toned suits, muted colour ties, and fitted shirts from English tailors, Hilditch & Key, became the hallmark of the Frenchman’s fashion-conscious approach.


Jagmeet Singh

A member of Canada’s New Democratic Party, Jagmeet Singh is unquestionably the country’s most fashionable politician - and quite possibly one of the snappiest dressers politics has ever seen.

Jagmeet’s Instagram is like a one-man fashion parade, featuring him wearing everything from a razor-sharp navy blue pinstripe to an effortlessly cool charcoal grey three-piece. Within the political arena, Jagmeet is known for pairing muted dark jackets with his brightly coloured Dhamala-style turbans, including eye-popping shades of tangerine, scarlet and mustard yellow.

Interviewed back in 2012, the Ontario politician also revealed he designs his own clothes. If further proof of his good taste was needed, Jagmeet was voted one of Toronto Life’s Best Dressed in 2013.