This is a well polished entry with lots of great pluses. It's a fun idea, the artwork is on point, the humour is very "Monkey Island" with the insult fighting.
The instructions and rules are overwhelming at first and I wonder if it would have been better to just use the "damage" and "defence" instead of proxies like wit.
The like to the theme feels a bit bolted on, but I love how original the hat idea is and how stacking up hats works as a mechanic and as a visual