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.
I've been reppin' this style since forever, 'bout time someone appreciates it--> For "sexy casual" love the grey sportcoat, navy/white gingham check shirt and dark jeans. Make sure he gets them hemmed! I will pin each item separately too