Stocking a bar doesn& have to break the bank. Start with the basics, and build from there. Assess your bar supplies each season and before each planned party. In the warmer months, think beer, white wine and light spirits.
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.