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.
The Getup: Early Fall Business Casual - Primer. Nice casual outfit, I would rather wear straight legged pants. Definitely change the shoes, if you wear those shoes with those pants, you're going to look like a clown.
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