Long story short - we made a trip to Payless and bought him new sneakers and winter boots.
I'm not going to count this because he cannot go out in sub-zero weather without winter boots - and he needs indoor shoes for school. We're going to donate his old sneakers which are lightly worn, to the Diabetes Foundation when they do their community clothing drive. I also bought a bottle of wine, but according to the rules, booze doesn't count. And here I was worrying about junior's boots!