To follow are a series of blogs created by Coutours. These help stitch together the fascinating fabric of London into a series of interesting tales and stories to showcase London in all its glory.
How many of you think of Winston Churchill as a style icon? I think he looked rather dapper in his
pinstripe suits and hats but he did have a rather interesting impact on the history of fashion. So let’s
take a look at some of his most famous outfits and fashion choices!
First up, the pinstripe suit; a classic that gained popularity in the 1920’s and has been in and out of
fashion ever since. Of course, when we look at its history, the most famous wearer of this particular
style was Winston Churchill (although there were a few bootleggers and those from the organised
criminal underground who also favoured this look!) Though he had a hard time holding onto money,
his clothes were always bespoke. More often than not, his suits were specially tailored by Henry
Poole & Co.
Interestingly, tailoring gave us the word ‘bespoke.’ Once a client had chosen a fabric, it was then
‘spoken for’ or ‘bespoke.’
The fabric of this particular suit was a flannel made by Fox Brothers, created exclusively for Henry
Poole. To this day, the company still makes this suit, which they call the Churchill style. Of course, it’s
made with a different fabric and for the modest price of £3,500.
But Winston Churchill wasn’t just in it for the fashion, in an age when television was just making its
entrance in mainstream households, how you looked was taking on much more significance. People
were used to hearing his voice on the radio, but they could now see him make his speeches in his
smart, dependable three-piece suit. Churchill, especially after his 1945 defeat, needed to reassure
the people that he was the right man for the job and I think his suit was an important tool to reassure
them that he was this man.
I think that although he is remembered for his cigar, which gave him an all-important point of
difference, it was his suits that defined him.
During WWII, so the story goes, Churchill noticed the bricklayers at his Chartwell estate wearing a
heavy boiler suit. Feeling inspired, he requested Turnbull & Asser to create a similar design from suit
material. Churchill loved the result so much, he ordered a batch of suits in different fabrics, including
Originally, he called them ‘romper suits’ but they were quickly associated with air raids as Churchill
and other citizens wore them specifically to go to bomb shelters. The suits were easy and quick to
put on over everyday clothes when the sirens went off and the suit was comfortable to wear in the
bomb shelter. This is why the design was dubbed a ‘siren suit.’
The siren or rather romper suit has made many comebacks. We saw them in the 1970s (although I
wonder if they knew that the original designer was Churchill and not YSL, they might not have been
as popular!) We have also seen its return more recently although most would not be suitable attire in
As much as Winston Churchill was known for his pinstripe suits and his “bulldog” image, his private life was quite different. Underneath that tough exterior, Winston was known for wearing pale pink silk underwear. Before you all start jumping to conclusions that he was into something saucy, this would be more like long johns or thermal underwear in style. Still, to paraphrase his wife, Clementine, they “cost the eyes out of his head.” His annual bill for silk underwear reached £80. This would be worth nearly £5,000 today - that’s a lot of pants!
Winston himself claimed the texture of the fabric was vital to his well-being: “I have a very delicate and sensitive cuticle which demands the finest covering.”
If you are wondering, he purchased his undergarments at The Army & Navy stores near Westminster.
The store is still there (it is now renamed House of Fraser) but sadly, they no longer hold a range of
pale pink silk underwear for men - well they didn’t the last time I looked anyway.
If you would like to learn more about the Churchills and their home life, please join our walking tour
‘In the Footsteps of Winston Churchill’.
As a tour guide and a lover of London, I will be writing a series of interesting stories about London; tales I have heard, places I have visited, tasty food I have eaten and delicious drinks I have enjoyed. Watch out for this every week or so.