Classic an understated. The khaki belt and the indigo blazer give a casual touch to the tie and the pocket square is exactly what all pocket squares should be - square and white. The brown leather watch band is classy too.
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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.