The Best Dressed Leader of All Time is Winston Churchill

Sir Winston Churchill was voted the Best Dressed Leader of All Time!

Pay close attention to the history of politics, and you’re likely to find that some of the world’s most prominent leaders also have a history of being exceptionally well-dressed. After all, you’ve got to be able to look the part if you have any intention of getting an entire nation to follow your lead. Many people consider Winston Churchill to be one of the most charismatic leaders of all time, and it’s difficult to argue with the fact that he also had a penchant for dressing well. And now, he is officially voted the best dressed leader of all time. Indeed, Churchill’s ability to lead Britain through one of the most tumultuous periods in world history was second to none, and the way he went about dressing further helped to cement him as being a leader that the “everyman” felt comfortable following. Understanding what made Churchill such a smart dresser is essential for today’s fashion-forward man, and the following are just a few aspects of his appearance that truly stood out.

The Blenheim and The Bow Tie

If Winston Churchill is known for any singular aspect of his style, it was his trademark bow tie, which he was seen wearing more often than not. Churchill was a huge proponent of the bow tie; especially those which were navy in color and featured a white polka dot pattern. His penchant for wearing this piece was so prominent that the navy/white polka dot bow tie came to be known as the “Blenheim,” which is allusion to Churchill’s birthplace. Many credit the resurgence of the bow tie in today’s fashion landscape to people such as Churchill who wore the piece unabashedly and were able to expertly incorporate it into ensembles of all kinds. It’s fair to say that without Winston Churchill’s influence, the Blenheim and the bow-tie wouldn’t be nearly as popular in the world as they are today. We thank Winston Churchill for that.

The Perfectly-Tailored Suit

Winston Churchill was an enigmatic figure, and he needed suits that could easily match his personality. Churchill worked with Henry Poole & Co. to find the perfect fit for his suits, who were able to create the chalk striped flannel ensemble that he was so well-known for wearing. The zip up “siren suit” was an especially omnipresent piece in Churchill’s wardrobe, and remains to this day one of the most unique pieces ever worn by a popular world leader. While Churchill would have undoubtedly remained a fantastic leader without his perfectly-tailored suits, they certainly helped to bring his professional demeanor to the forefront. Muammar Gaddafi could of definitely taken some lessons from Churchill in the charisma and style department.

Takeaways for the Modern Man

Modern men have a lot to learn from the way Winston Churchill approached fashion. For one, those who have never tried to incorporate a bow tie into their ensemble can get a lot of mileage out of experimenting with this piece, as it can look quite sharp when paired with a modern-cut suit. Prominent men should also ensure that they work with a good tailor in order to find suits that will truly fit their figure, which can help to increase one’s air of professionalism by a rather large extent, and doesn’t have to be expensive. Take a lesson from Mr.Churchill and you might be considered the best dressed leader in your own circle.

To see a brief breakdown of our Top Five Best Dressed Leaders click here.

You also might like our breakdown of the Worst Dressed Dictators of All Time by clicking here.


Your Bows-n-Ties.com Fashion Team