Maybe his diary and pencil and a picture of Earth

A tube of paint or a brush

A piece of paper, that is a love note

An asteroid from Neptune, a gift

Better self esteem, nope

Insecurity, yes

Perhaps a hair tie?

Or...a feather from his wings?

Money?

No, not a safe place to keep money

The most important thing of all in his pockets, is the ring, not the ring around his head, a stored ring, for a certain someone whos name starts with E and ends with H...