Sir Winston Leonard Spencer Churchill = /ˌbo͝oləvärˈdi(ə)r/

by Kim Steele

On the date of our first anniversary with an amazing 120,000 site visits, I raise a glass and toast all boulevardiers and especially the ones who contributed to this uplifting and informative eMagazine.  Congratulations to us all!!

~Kim Steele, The Boulevardiers Founder & Publisher


Young Churchill


Often viewed as an indomitable force in European politics, Sir Winston Leonard Spencer Churchill is a complex figure who suffered many vagaries in his life and career.  Born to aristocracy, Duke of Marlborough, he was not a great student but succeeded as he said, in the areas that interested him -significantly, history. He was not a stellar enough student to be granted admittance to Cambridge or Oxford, but he pursued his education at his own pace, in fact he failed three times to gain acceptance to the Royal Military College and then only as a cavalry position. Winston loved horses and played polo until he fell a final time in his fifties. Throughout his life he focused on his sartorial spender, starting at a tender age, having garments tailored to him and frequently requesting fabrics from his mother in London accompanied with drawings of blomers and the like.   He held many positions governmental in GB, including Prime Minister twice (1940-45 and 1951-55). Churchill suffered many defeats along the way, including his failure to regain office in 1946, after his great leadership and alliance with the US in WWII.

On a number of occasions, especially during what he called the ‘Wilderness Years,’ 1930-1940, when Churchill was ostracized from government, by switching from the Labour party to the C0nservative, he suffered from deep depression, which he called the ‘Black Dog.’ He fought this his entire life with resounding results. He held two very unpopular positions during this difficult period; first his resistance to the abdication of Edward VIII and secondly, the call for resistance to Hitler, as he was gaining power in the mid-1930’s.  Both positions proved insightful.  Only after the invasion of Poland, did the government agree to build up its military that he had advocated years before. He was then asked to become the Prime Minister in 1940 by all three parties and George VIth.


Winston Churchill 1896,







Churchill proved himself a soldier of valor in a number of campaigns. He saw action in British India, the Sudan and the Second Boer War.  His downfall was the fall of Gallipoli because of poor strategy. He had been a warfare tactician since his early youth when he amassed over two thousand play soldiers that he arranged in battles on his childhood floor. Due to his extravagant lifestyle that plagued his finances his entire life, he moonlighted as a war correspondent for British publications, as well at US publications.  From his early adulthood, his taste in clothes, cigars and expensive champagne threatened his solvency.


Winston Churchill, photograph by Alfred Stieglitz, 1940



Winston Churchill and Robert Gordon, 1912,



Churchill’s slippers,


Churchill had style, and even though his choice of undergarments might not suit his public image, comfort was his first concern. The silk was an extravagant expense, justified by a therapeutic application toward Churchill’s persistent skin problems. But, be it in the trenches of Antwerp during World War I or sitting alongside F.D.R. and Joseph Stalin, Churchill always dressed in the finest everything. Photos of Churchill are punctuated by how striking a figure he cut, his clothing tailored just so. His suits are so well-regarded that his tailors, Henry Poole & Co., one of the oldest and most respected bespoke tailors on London’s Saville Row (and therefore, the most respected in the world), reissued the cloth used for Churchill’s famous chalk striped flannel suit, woven by the same English mill that made the material in 1936, for the centenary of Churchill’s first order with the iconic shop.


Winston Churchill with fiancée Clementine Hozier,


Churchill was a dutiful father and husband.  Despite that he was absent many years from his home front, he frequently wrote endearing letters to his wife, Baroness Clementine (Hozier – family name), and to his family.  Winston & Clementine suffered various diseases common at that time.  They lived very independent lives, she often vacationing at various villas in Italy and France of family friends’. The Churchills  moved from numerous homes as their liquidity varied. Winston sired five children, with one death at an early age.



Winston Churchill playing polo, 1925





Winston Churchill © Estate of Yousuf Karsh, 1941


Winston’s parents, particularly his father, were not a loving and supportive set. In fact he was quoted as never speaking much with this father who died at the early age of 45.  His mother was an American, which gave him a special kinship to the US.  She married several times, often to much younger men. His savior was his nanny, Mrs. Elizabeth Everest. He strived, unsuccessfully, to gain his fathers approval, which he in turn provided similarly to his son, Randolph.  Randolph dropped out of Oxford against his father’s objections to pursue a life as a journalist.

In the book, Churchill Style, by Barry Singer, Churchill’s proclivities for extravagance and indulgency are well documented.  But the soft underbelly of a man, feared by politicians and tradesman, which was legendary, paints a tender and sensitive poet. He pursued painting as a past time, to some success, even writing a book on it.  He was so hands on in every front, he was invited to the Bricklayers Union due to his skilfulness. Churchill was a prolific writer, a prolific reader, and the only PM to gain a Noble prize for Literature.


Winston Churchill signature


Singer describes a man focused on so many details, that it seems unimaginable that he could accomplish so much.  Between working from bed in the mornings, to lavish lunches where Winston drank a bottle of champagne, to five o’clock naps, more reverie at dinner and cigars though out the day (as many as five), he often entertained guests with speeches during dinner only to retire to his factory to work till three in the morning, on his writing and speeches. Churchill was first and foremost a grand orator.


Churchill & Eisenhower,


Winston Churchill riding to hounds, 1948,










Despite the popular historical image of an overweight, statesmanlike Churchill smoking a cigar, the politician was lithe and fashionable in his youth. Known for his love of fine clothes, between 1895 and 1900 Churchill was thought to have run up the modern equivalent of £30,000 in tailors’ bills.

Another of his passions was book collecting. He would drive up exorbitant bills at his two favorite book dealers* despite Clementine’s abjection and reminder of their delicate finances.  He was not to be reigned in.

“Churchill’s creative method was at the bottom gastronomically social,” states Singer. His taste in clothing was very peculiar and specific. He often, while entertaining and working his ‘factory’ standing at his desk, wore his ’carpet slippers.’ He in fact created an outfit he called his ‘siren suit’ which was a baggy blue jumpsuit made from parachute silk. Churchill was not always extravagant. He unfortunately was in New York on Black Thursday in 1929 when the Market collapsed, viewing a man jumping past his hotel window to his death. He lost much of his wealth, as did many people. In order to compromise his expensive taste in Cubanos, he found a ‘cheap’ cigar in the ground floor of his friend’s office, financier Bernard Baruch, The Equitable Building, marked ‘Royal Derby.’  There is a receipt for his ordering one thousand. He kept them in a small room in Chartwell, in boxes marked “Wrapped,” “Naked,” and “Large.”  Despite receiving many cigar cutters as gifts, Winston did not use one.


Chartwell House,

Winston Churchill behind the wheel of his Wolseley, 1925,



Bad timing it was, after bouncing around various properties for years in London, Churchill purchased without Clementine’s approval the love of his life, Chartwell House, a country property after much bartering.  It required much improvement; in fact as early as 1931 he closed down the home and moved the family to a small cottage on the property to economize. This only drove him to lecture and write more fervently. Two tours of the United States and Canada ensued.  He did make a splash in Hollywood befriending the ‘Bolshie’ Charlie Chaplin, and hobnobbing with the Movie set.


Churchill & swan




Churchill & daughter Mary at her wedding,




Every detail of Winston Churchill’s attire was orchestrated. “Mr Churchill was always dressed somberly with a bow tie and felt hat” recalled a realtor Henry Harding. His watch was a Breguet pocket watch, nicknamed ‘ The Turnip’ due top its shape, secured to his pocket by  a silver head of Napoleon. He rubbed elbows with all sorts of nobles, including Coco Chanel to whom he told Clementine he “took a great fancy to.”



Winston Churchill paints at his easel, 1948,


Winston Churchill, Coco Chanel, and his son Randolph,


He was also passionate about his automobiles.  He always owed more than one. The ‘big car’ was the Rolls-Royce, which was eventually bullet-proofed, the ‘little car’ varied from a two-seater Wolseley to the upgraded Landaulette. he popularized the gin martini:



 Gin served in a martini glass, usually shaken over ice.

Made popular by British Prime Minister Winston Churchill, who when once asked how much vermouth he would like in his martini, was quoted as replying…

“I would like to observe the vermouth from across the room while I drink my martini.”


Winston Churchill and Lord Beaverbrook in 1958,


According to Sir Winston’s close friend Lord Beaverbrook, (William Maxwell Aitken), the great man was always either “at the top of the wheel of confidence or at the bottom of an intense depression.” He was notorious for monologues that could last for up to 4 hours or longer. He often distressed his staff by meeting with them while dressed in nothing but the pale pink silk underwear that he had personally tailored. He would even walk around his house completely undressed or insist on conducting meetings from his bathtub. At his death Churchill left 15 tons of personal papers. Most of his income was derived from his writing, and he wrote countless articles, and 43 book-length works in 72 volumes.

Winston Churchill will be remembered as a great statesman, though some accuse him of colonialism and warlording, his strengths as a  tactician will establish him as one of the great  leaders of the twentieth century.  As well, Churchill will be remembered as a Boulvardier who set the tone for living the ‘good life’ while being creative and productive. There is a wonderful exhibition I had the pleasure to visit at the JP Morgan Library in New York on the papers of SWC.  A well-curated selection of his documents, many handwritten in an illegible hand, are accompanied by a most moving selection of videos that exemplified this oratorial prowess, especially the speech resisting Hitler’s carpet bombing of London…extremely moving.  It closes September 23, 2012.  I highly recommend it!



Winston Churchill

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