Even 50 years after his death, Britain’s most stylish prime minister is still looking good.

There’s a quote among the legions of juicy aperçus attributed to Sir Winston Churchill that seems to sum up his personal style: “I am a man of simple tastes. I am easily satisfied with the best.”

Half a century after his death, amid a slew of new books and TV documentary tributes, it's clear that our fascination with Sir Winston shows no sign of abating. And a large part of that fascination is the sense that, behind his stellar achievements – revered statesman, decorated soldier, accomplished painter, winner of the Nobel Prize for Literature, and, oh yes, arguably the greatest wartime leader of the 20th century – is someone who lived life on his own exacting terms.

“He wasn’t a dandy in the classic sense, but there was certainly an artistry in the way he conducted himself, from his dress to his accessories,” says Mr Barry Singer, author of the book Churchill Style. This, after all, was a man whose valet wielded a silver-mounted Asprey thermometer to test the temperature of his bathwater, and who always wore pale pink silk undershorts and vests bought in bulk from the Army & Navy stores, ostensibly for his sensitive skin, but which, according to his wife Clemmie, “cost the eyes out of his head”. From the start, Sir Winston had a theatrical sense of himself: “We are all worms,” he once said, “but I believe that I am a glow-worm.”

He was born in a bedroom in Blenheim Palace, his father being the third son of the seventh Duke of Marlborough; his mother Jennie was an American heiress, one of the Dollar Princesses who crossed the Atlantic looking for a title on which to hitch her fortune, and Sir Winston was proud of the US strain in his lineage and the outsider status he felt it conferred on him (he was a Conservative, Liberal and Independent over the course of his career, and seemed happiest in the latter role).

He went to top English public school Harrow, then to Sandhurst for military training, and he showed an early talent for living beyond his means, with his father berating his “happy-go-lucky, harum-scarum style”. He skirted bankruptcy more than once in his life, and pulled himself back from the brink thanks to his ambition, energy, resourcefulness and seemingly boundless self-confidence.

Mr Churchill became an MP in 1900, and cultivated the haute Edwardian look that became his trademark. At a time when most men stuck to a utilitarian uniform of three-piece suit and bowler hat, he now indulged his long-held taste for fine clothes (even while at Harrow, he would send sketches to his mother indicating the kind of garments he wished to be sent: “One pair of knickerbockers, one jacket, one waistcoat, all of the same stuff...”). His breeches came from E Tautz; his suits and coats from Henry Poole & Co; his canes and umbrellas from Thomas Brigg (later to become Swaine Adeney Brigg); his hats (mainly homburgs) from Scotts, or Chapman & Moore; his boots from Palmer & Co; his grey antelope slippers from Hook, Knowles & Co; his travel trunks from JW Allen; and his pistols and rifles from John Digby & Co.

In the classic tradition of the English gent, he would stretch his credit to breaking point, with an unpaid-bill trail going back years. He’d taken up cigars at 15, buying 200 La Corona or Punch habanaos at a time from Dunhill or J Grunebaum (the redoubtable glower in Mr Yousuf Karsh’s legendary portrait of Churchill is the result of the photographer impulsively snatching his sitter’s cigar from his grasp just before clicking the shutter), and complementing these with Pol Roger champagne (favourite vintage: 1928) from Randolph Payne. On sipping the latter, he rhapsodised, “the nerves are braced, the imagination agreeably stirred, the wits more nimble.” He was also partial to Johnnie Walker with soda and no ice (he once disdained the offer of a mid-afternoon cup of tea: “I have made it a rule of my life never to drink non-alcoholic drinks between meals”).

At Chartwell, his Kent country house, Sir Winston kept black swans, stocked his pond with orfe (a golden-orange carp supplied by Harrods) and enthusiastically took up bricklaying, becoming so accomplished that he was invited to join the Union of Building Trade Workers.

But his most striking stylistic innovation was his wartime “siren-suit,” a self-designed zip-up onesie that could take him from war cabinet meeting to air-raid shelter with utilitarian ease. He had Turnbull & Asser make up various iterations of the garment, including blue serge (for daywear), red, blue and green velvet (for evening), and smock-style (for painting). Sir Winston’s military assistant General Hastings Ismay could have had this outfit in mind when he said of his boss: “He venerated tradition, but ridiculed convention.” That, according to Mr Singer, is why Churchill himself remains an object of veneration: “He unashamedly carved his own path – he would have scorned focus groups or any idea of political expediency. He mixed his own cocktail out of it all.”

Sir Winston was famously imperturbable. On his first visit to the White House, in 1941, he was dictating a speech in his room, post-bath while swathed in a huge towel. As President Franklin D Roosevelt entered, the towel fell to the floor, leaving the British premier naked. “You see, Mr President,” he deadpanned, “I have nothing to conceal from you.”

He often entertained until the early morning, and was prone to dance, drink and eat (limpid broths, foie gras, Yorkshire pudding, chocolate eclairs) with equal abandon. When giving his first budget day speech as Chancellor in 1925, he took a swig of something suspiciously whisky-like at the dispatch box, saying: “It is imperative that I should fortify the revenue.”

He came close to ruin many times, but refused to skimp on home comforts. “We live very simply but with all the essentials of life,” he wrote to his brother Jack from his country house in 1915. “Hot baths, cold champagne, new peas and old brandy.”