Odd thought on pocket squares: I like to just tv-fold mine (including the coloured silk ones), shove them in the breast pocket, adjust for proper height, and leave them there until the inevitable day when I think that the PS is so atrociously out of step with the rest of the day's ensemble (or with the season, or both) that I HAVE to change it ... so I select a new one and repeat the procedure. Now, I know that the received wisdom about PSs is that you should select the day's PS to be "just right" for the day's outfit (not matchy-matchy, more somewhere in the complimentary--pleasantly-contrasting spectrum) and then artfully arrange it in the breast pocket to look like you just casually shoved it in there.
The attire of world-class politicians is certainly not happen-stance or whim. I fully expect that the clothing choices of modern American presidents (and electoral challengers, for that matter) are the product of vast amounts of psycho-analysis and focus group testing to get "just the right image/message." Ditto for other major western nations. Gone are the days when JFK woke up, thought to himself "I wanna dress macho and presidential so I can nail Marilyn again", and grabbed whatever was in his wardrobe.On the other hand, I am fascinated by the exquisite grooming and neat, pressed, and careful dress of some of world-class politicians when you see them in person. There is something artificial about it, especially when you first meet them. But I have to admit that there is something about that seems to add to the charisma, overall attractiveness. Maybe it is as if they have dressed up to "talk to me" because I am important, or something like that. There is definitely something subliminal and symbolic going on, methinks. Also, I have no ability to that well-groomed and put together just so, not even for an hour. Much less hour after hour. That impresses me!
Not all great politicians are so. I would say that Churchill was not. Maybe me had a studied nonchalance!
By the time he reached 1939 and until his death in 1965 ... the period from which we draw most if not all of our recollections of Winnie ... Churchill was no doubt past caring about looking stylish. I suspect he wanted to look the way he wanted to look, and it happened to be stylish. I suspect in his youth he was stylish and over the years developed a good "inner compass" for style ... which served him very well in his brandy-fuelled final decades of not giving a damn.
(Doubtless he gave a damn that he met his own standards ... but as for whether or not his standards accorded with popular fashion ... bah!)