Churchill Style - The Art of Being Winston Churchill

Churchill Style Book Review

Winston Churchill is both one of history’s greatest and most stylistically evocative figures.  The British statesman served in numerous government posts of one of the world’s great imperial powers at key moments during the course of the 20thcentury.

Churchill Book - My African Journey Cover

Churchill Book – My African Journey Cover

He was called to head the Admiralty (navy) during World War One, serve as Secretary of State for the Colonies during the creation of the Irish Free State, take charge of the Exchequer (treasury) during the tempestuous 1920s and, finally, to reside at Number 10 Downing Street as Prime Minister during World War II (a post to which he would be recalled during the Cold War).  He also wrote numerous books that included several multiple volume histories and delivered countless rhetorical masterpieces in the House of Commons.  But then there is also the exuberant Churchill of great style, the Churchill that was “easily satisfied with the best” in creature comforts ranging from cigars, scotch, automobiles, country homes, food and champagne, right down to his silk underwear and pajamas.

We often portray style and substance as being in tension if not outright incompatible, but Barry Singer’s Churchill Style: The Art of Being Winston Churchill illustrates how Churchill’s lifestyle furthered his substantial career.  As a bonus, the book’s details add a good deal of gloss to the Churchill story, helping us to feel as if we know the great man just a little bit more intimately, just as we know our friends by the brand of beer they drink or the type of car they drive and the other everyday items they love that we come to associate with them.

Churchill Illustration

Churchill Illustration

It’s as if Yousuf Karsh’s famous photograph of Churchill had blossomed into glorious color. I hope you will enjoy today’s book review of Churchill Style.

The Book

Airman Churchill

Airman Churchill

Much of Churchill Style does concern itself with the items most famously associated with Churchill: the ever-present cigars, bow ties, homburgs, dark suits, and whiskey and sodas, the seemingly endless amounts of cognac and champagne, and his ever present, trademark “V for Victory” hand sign.  Singer, the owner of the Churchill-focused Chartwell Books, covers Churchill’s homes and his past times, such as his polo playing, painting, and reading.

Readers will be treated to the intimate details of Churchill’s life, often hinted at in other works, via such exhibits as railroad service instructions telling stewards precisely how to stock Sir Winston’s private railway car (canapés, coffee, tea, Johnny Walker Black, Martell extra cognac) and serve his breakfast (tea, juice, eggs and sliced meat), detailed book orders, and the ubiquitous tailors’ bills that were an ever-present irritant in the life of a Victorian or Edwardian gentleman.

Churchill’s Clothes

Churchill’s wardrobe is also covered in extensive detail.  Singer explains the origins of Churchill’s preference for bow ties, relates the criticism Churchill received from Tailor and Cutter magazine for his choice of wedding apparel and explains his penchant for the odd looking “siren suits” (front zippered jump suits).  A full blown “Churchillian Shopping Guide” is appended for those who wish to purchase their clothes and accessories from those same shops frequented by Churchill that remain in existence.

True Style

In the Air

In the Air

These are, however, only the small and superficial elements of a much broader and meaningful conception of style, namely the approach by which Churchill rose to power in just the right place and at the right time to play perhaps THE critical role in the history of the 20th century.  For Churchill, style and substance were not competing elements or even in tension.  Churchill’s style was a vital aspect of his very being and it is the book’s subtitle, The Art of Being Winston Churchill that best conveys the book’s principle value by describing how Churchill’s lifestyle served to sustain his meteoric, if highly volatile, political career and the writing that ultimately earned him a Nobel Prize.

Churchill's Velvet Slippers

Churchill’s Velvet Slippers

Picasso himself remarked that Churchill could have earned a living by his landscapes.  For Churchill, however, painting provided a much needed psychological break from the burdens of leadership.   He even went so far as to claim that he couldn’t have born the strain without painting as one form of self-expression that he found necessary to live.  Less well known among Churchill’s past times was his passion for horses, both in the form of playing polo and owning race horses.  He also did not shy from manual labor despite his illustrious upbringing and was proud that his brick laying skills developed to the point of earning membership in a bricklayers’ union.  The never ending projects undertaken to improve Chartwell, his country home, were also doubtlessly a great source of diversion and stress relief.

Churchill in Spy Magazine

Churchill in Spy Magazine

Singer does not neglect the other vital roles that Chartwell played in his career.  A day away from Chartwell was wasted according to Churchill, and it was both the center of his political life as well as his retreat from it.  A decaying structure dating back to the Elizabethan period, Chartwell was a money pit that helped keep Churchill close to bankruptcy for much of his life.  As Singer puts it, “His singular gift was a stalwart ability to live as he wished, even if it was often beyond his means.”  Yet, it was the need to finance the lifestyle that Chartwell entailed that drove much of Churchill’s journalism and writing.  If necessity is the mother of invention, Chartwell certainly played a major role in Churchill’s literary output.

To be clear, one does not have to emulate Churchill’s particular lifestyle to lead a life of substantial accomplishment.  For at the end of the day Winston Churchill’s style was more than a mere accumulation of homes, horses and autos.  The cigars and brandies were, in fact, mere accoutrements and a fascinating diversion for readers.  At its heart, writes Singer, the essence of Churchill’s style lay not in mere things but in “the ambition, the energy, the resourcefulness and the boundless self-confidence…his infuriating conviction he was bound for greatness, as well as fearlessness in pursuing it…”  It was these last elements that allowed him to survive political catastrophes that would have felled a lesser man.



His career could well have been ended (undeservedly) by the failed Dardanelles campaign in 1915, with which he was closely associated or as a result of the decision to return Britain to the gold standard, an ill-fated endeavor he oversaw as Chancellor but of which he did not approve.  As a result his career was viewed as being in such a shambles that when asked by Stalin himself about Churchill’s political future in 1932, his nemesis, Lady Astor, replied simply, “Churchill?  Oh, he’s finished.”


Diverse audiences will find much to enjoy in Churchill Style.  While it is not the ideal volume for a reader wishing to read only a single book about Churchill, it will serve to whet the appetite and make most neophytes wish for more.  Alternatively, dedicated Churchillians will revel in Singer’s numerous details about Churchill’s personal life and the list of Churchill’s chief purveyors still in operation should they wish to imitate the great man’s lifestyle.

Churchill Style Book Cover

Churchill Style Book Cover

All readers will appreciate Singer’s highly intelligent observations about how Churchill’s style contributed to, and was ultimately an integral part of his brilliant career, putting to rest any notion that one need choose between style and substance.

The book can be purchased from amazon for $15 (for $12 you can get the kindle version) or directly at the author’s Chartwell Bookstore in NYC, which is specialized on all things concerning Mr. Churchill. For more information about the book, including screenshots and a blog, visit the official Churchill Style website.

Since the book is truly great, we added it to our 100 men’s fashion book guide.

This review was written by our fellow reader Alec Rogers. If you want to contribute to the Gentleman’s Gazette as well, please contact us.

1 reply
  1. The Trad says:

    Wonderful review. Great book. Singer’s approach is entertaining enough for us newbies reluctant to crack a six volume history of war but bright enough and loaded with images for WSC cognoscenti.

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