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.
Tweed, tweed tweed god I love tweed. Not just for the millionaire horse owners anymore. Tweed just scream class. Throw in a flat cap and a scarf and you're ready to take on winter in style. -Not a big fan of tweed but looks good here.