Jester Hat Pros:
Very squishy, moves like jell-o, very entertaining
Kinda funny.
Fits well with almost any color
Jester Hat Cons:
Looks stupid with some sets or colors.
Santa Hat Pros:
Jolly, fun, wiggly but firm.
Always noticed by people, never a bad thing to have
Santa Hat Cons:
Only works best during winter, where people will most likely point it out
Too simple of an item, doesn't fit with much
I would want the Santa Hat, if it helps.