There should be one thing abundantly clear to you when you look at the recent celluloid incarnations of Winston Churchill on screen – most recently by Gary Oldman in Darkest Hour – which is that for all his greatness, Churchill was not really built for suits. In fact, he was a tailor’s nightmare. Slumped shoulders, arched back, engorged gut; these are all challenges that, in isolation, would test the cutter's skill in mitigating physical factors. His unflattering physique was the one thing he couldn’t talk himself out of. “Stylistically, he was very much in his own realm, but figuration-wise it was a challenge,” says Simon Cundey, Managing Director of Savile Row heavyweight Henry Poole, Churchill’s tailor of choice. Currently, you can find a selection of resurrected looks of Churchill that were made for Gary Oldman in Darkest Hour, in the window of Henry Poole.
This was not always the way. Churchill, a military man – cavalry to boot, whose uniform was famously flattering – can be seen on tour or in civvy street cutting quite the dash. If we accept the premise that his sartorial legacy is adjunct to how we have immortalised him on statues and signs on pubs, then his later years are what we should focus on.
Furthermore, what is impressive is that Churchill managed to carve his way into style folklore when spending his senior political career more or less attached to the hip of Anthony Eden, the best dressed politician of all time. He was Prime Minister during the war and that made all the difference. No matter what everyone else did, so long as Churchill emerged from Number 10, Downing Street with a stiff collar, his Lock & Co. bowler or Homburg on his head, pressed suit, cigar and highly polished shoes, then the ‘keep calm and carry on’ spirit prevailed.
Churchill no doubt gets mileage from his legend, the bulldog-faced portraits that were a symbol of defiance and Britain’s courage. His three-piece suit with the bow tie and pocket watch was unquestionably a becoming look. A regular necktie could have acted as an arrow to his tummy and the waistcoat corseted his shape and allowed for the jacket to focus on draping round the pronounced curve of his nape.
He was very much a man of occasion and had outfits to suit each one, so what follows is a breakdown of his most notable styles, during and after the war, and how he mastered each of them.