I think Marc Johns has nailed it. This is exactly the kind of whimsical hat an ampersand would wear. Here are some other suggestions punctuation/headgear combos:
- colon wearing a bowler hat
- semi-colon wearing a flat cap
- question mark wearing a fedora (everyone knows question marks are hipsters)
- exclamation point wearing a pickelhaube
- hash tag wearing a Pope hat
- umlat wearing a miner’s helmet
Feel free to add your suggestions in the comments!