He's racing to get to the bus and get to work on time...learning to schedule time.
Yesterday, I showed him how to use the car pump to add air to the tires. Some months back I saw this coming and made him take that bike in to fix the cranks and tune the bike. So the bike is in good shape but...both tires were flat (and there was a spare tube sitting there). Running late to the bus in the rain.
The warm hat and gloves are good ideas. I don't plan on buying anything...just 'giving him the tools to survive'. After he went to bed and his shoes were dried out, I sprayed them with waterproofing.
Although, I'm not totally sure what he'll need yet.