Originally Posted by Caustic Man
Generally speaking, yes. For instance, wearing a business appropriate necktie with a dinner jacket doesn't casualize the dinner jacket, it's just incongruent. I think you can categorize accessories such as shirts, shoes, and ties much more than you might think. This isn't to say that there aren't exceptions, but I think they would be relatively few.
Agreed. I also think you have the correct premise with this thread--that we're better off thinking about the history and context of application than about absolutes related to the type of item being considered. "This doesn't make sense as part of an informal ensemble" is much less likely to result in silly absolutes than "suits don't go with derbies" or "white linen doesn't work with odd jackets."
How do you categorize, though? Is the categorization a case-by-case consideration, or a litmus test based on the presence or absence of a feature?
For example, some posters, with their most accomplished exemplar being @Pliny, believe that neat tie patterns categorically belong with suits and not odd jackets. It's not clear if he means that they fall in the "casual" category but belong with non-business suits, or if he firmly associates them with the "informal" category of clothing. A case-by-case or composite approach would say that an ancient madder or wool challis with large, complex patterns is "casual" while a plain weave silk with dots is "informal," while a litmus test would say that neats belong in one camp or the other.
The nerd in me is getting excited, but using your categories of formality, at first glance I think you could further divide those who think about sartorial coherence into four categories: categorical absolutists, categorical permissives, composite spectrum-ists, and idiosyncratists. I'll elaborate once I've let that idea breathe and decided if I'm full of shit or not.
Edited by heldentenor - 7/29/16 at 3:20pm