Plaid Wool Jacket, Polka Dot Scarf (This is most probably too preppy for John, but I could see elements of it working for him. The vest and scarf and instead of the blazer take that pattern and put it on the pants.
From GQ: "Cardigan" Is Now Spelled C-O-A-T Why have cardigans been bulking up like Dwayne Johnson all season? So they can be your outermost, always-on layer Cardigan * Nothing cozier than a chunky sweater. But remember: Chunky doesn't mean baggy.