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.
This is an amazing color palette. I love the colors used in this outfit, it is put together nicely and also fits into my career path. I want to design clothing that fits into modern life and the color scheme of every season.