Warning: Spoiler! (Click to show)
Agreed - I dislike them alone with no jacket (although I used to wear that 20 years ago), and I also dislike them not matching with a business suit. But as you said, this is exactly how it's supposed to be done. :)
Re. NYI's tie, I think it looks OK as the shirt and tie together contrast so much with the rest of the components. But I do agree that it might work better with another colour group brought in there - if not the tie, then at least a PS. On which point: I'd appreciate your view on my hurried and non-contrasting choice today - too dull?
His outfits hark back to what Bogart and Cary Grant wore among others.