Harrington and drainpipes? You're showing your vintage my old mucker!
I think the Laurelhurst is a lovely balance of the elements you mention, and I like all Justin's loafers actually. I have a similar tassel from elsewhere, and a rather traditional burgundy penny from France that is, I suppose, the least informal and most classic of loafers. For me, the Prince Albert is the king - forgive the pun - and I will get some once the piggy bank permits.
Your concern about how to wear them is fair enough. Personally I never wear loafers with a suit, rarely even with an odd jacket and no tie. For me they are indeed outdoor slippers, and work with no tie, linen trousers, chinos, perhaps cords, and a casual shirt or polo. However, if you want something easy and comfortable, but a bit more respectable with a tweed sports jacket or a soft suit, then I suppose you're left with a single monk or a lazyman. There are millions of the former - Justin is coming with his own good looking range shortly, I just read - and for the latter, Anthony Cleverleys look rather special, and of course G&G and many others do them. At a more experiment-friendly price point, these are in the Howard Yount sale. (But only if you've diddy feet)
Haha, indeed they are ageing showing one's vintage. That said I was a second wave mod, keen on Specials after northern soul. There, that should test your references!
Loafer stuff, you're quite right. even my C&J monks have to be hooked up carefully with the right fit. I do know this, from some time back, is not the best example
Cleverleys and of course G&G are excellent, those HY look cool too but rather like a C&J!