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.
Striking the right tone for Fall. Combining pattern and textures successfully is achieved by varying scale, but maintaining a tight color palette. This look was executed by mixing subtle blues with rich golds and reds.