Great post and comments.
I'm not sure I'm experiencing a new direction, but I have been attuned to the need for juxtaposition of my classic items, trousers, with some more "ladylike", pretty, not sure what word to use. Slightly dainty, for me, but not twee. So sometimes I think I nail it and sometimes things look too stodgy, frumpy (sorry for more loaded words).
The BR shirt with the ruffled stand collar is really fun for me as it works differently with a classic blazer than would a typical shirt or even most knit tops. For me, though, it is not simple a ruffle, but the collar will stand up abit , yet is not actually "popped", and is not buttoned up tight. So the collar does not get as smooshed, either.
I'm actually having trouble styling the plaid blazer (shown) in other ways because it looks TOO plain and classic with work trousers and several tops I had planned for it.
The flounce tops are not very "flouncy" but look just a bit "prettier" with a trouser, and also are meant to be left untucked, which is hard to find sometimes in wovens.
Footwear is similar--if I wear a classic loafer it looks better with a slightly more ladylike pant, or I even like them with pencil skirts. For more classic trousers, I like a refined boot or a shoe that has something a little more "feminine" about it. That can be hard without doing pumps, so just the right flats are HEWI's for me.