Reb,
“– to the point that after he discussed the topic with them, he stopped sleeping a sukkah himself)! ”
I don’t know which nonsense you have been reading, asides the heter of not sleeping in a sukkah is mentioned in the Rema, this is totaly fabricated. Rav chaim and all his talmidim sid indeed sleep in the sukah.
“The Chofetz Chaim wore a cap (kashket) – there are pics. He did not wear a Borsalino! When did a Litvish hat become “The Look”? A tie is “required” for bnei Torah – when did that “requirement” start (chassidic bochurmin. kollel men and rebbes don’t wear them!)?”
The same way Chassidi Admorim decided wearing velvet and fur coats are part of yehadus or wearing silk etc. Not The Rambam nor the Beis Yosef nor the Rema wore black velvet hats.
אלא מאי,
Each group, segment or region decided to stop the clock at a diff time or era, the is NO specific mesorah in klal Yisrael how exactly your hat has to look like. With a pinch or without. Chabad decided to stop the clock in the 1930’s and the Yeshivish in the 50’s not so Yeshivish 60’s etc
E.g. Rav Eliezer Silver zl decided to stop as the early 1900s wearing a stovetop hat. Same as Rav Itzele of Ponovizh..
The rest is all שטיות the fact is that ia how a Ben torah nowadays dresses so behold that is the dress codw. Same with chassidim. There is nothing more holier in a velvet hat than a hat with 2 or 3 pinches ..or with a tie ir without…
A שמחת פורים whatever hat you decide to wear..