Have just read
this post by innocentsmith which involves among other things the class distinctions in English society which make Jeeves/Wooster a ttl transgression, and two several thoughts:
1) That's at least part of why Lord Peter/Bunter never ever crossed my mind until somebody else wrote it, and why I still don't endorse it
2) It's what makes Aubrey/Maturin so right - Stephen's the only one on the ship Jack could turn to, although of course in their case the vicissitudes of rank intertwine with and complicate the questions of social standing
3) See also Sharpe/Harper, wherein they are of the same social standing, but differing ranks, and things are even more complicated, but Sharpe doesn't give a damn
4) Simon's utter disregard for such things is part of his love. Of course, there's also the question of - what class is Simon? He acts like, is regarded as, a toff, but that doesn't necessarily mean he actually has the upbringing and background. It is highly possible, even likely, that Simon Templar's entire life is an act*, from his name to his carriage; and so, as he's probably not even of the class he assumes to be (Patricia Holm actually is, and the fact that everyone simply accepts that Simon's upper class too is a very good testament to his skills at deception), he's highly unlikely to give two shits about apparent/supposed class distinctions between himself and anyone else. Plus, how would his status as a wanted criminal (although, to be sure, after he got a pardon from the King himself at the end of Avenging/Knight Templar he's got an official record as shiny as Killick's silver) affect his status as a Bona Fide Toff? I don't know.
This might not be very intelligible
* In fact, if this is true, that fact alone can make you comprehend him as a character and as a person. Given the society in which he was raised, in which You Are What You Are Born, his decision at a young age to say "Bollocks to that" and go out and say I Am What I Decide I Am is all you need to know to know exactly who and what he is. The utter disregard for EVERYTHING society says ought to happen is expressed in every facet of his character, every act of his behaviour, and while anyone might decide to be a criminal - Bertie Wooster steals cow-creamers, Rupert Psmith nicks jewelry and goes to great lengths to cover up supposed crimes of his friends - that's nothing, you can do that sort of thing and still be a respectable young gentleman; disregarding the inherent class structure and defining yourself as something that exists outside it by your own rules is Social Transgression On The Grandest Possible Order. Everything else about him springs from the same personality that enables him to do that with an utter lack of conscience and absolute self-confidence.