@Dustcan  

 
You’d think someone smart enough to learn the deepest secrets of creation, and learn how to impose his will on reality and make the world warp and flow like melted wax to suit his whims, would think things through a little further, yes.
 
But it’s a long tradition in Western literature that, when it comes right down to it, your average “wizard” is not the sharpest crayon in the box. There might be exceptions here and there, but just read (for example) Howard and notice how many “evil wizards” meet their ends when Conan or King Kull or Solomon Kane kicks down the door, rescues the girl, and lops the “wizard’s” head off in mid-cackle.
 
Evil wizards never read the Evil Overlord List.

@Background Pony #AC7D  

 
To be entirely fair, we don’t know that he’s not being ironic. If I were a wizard I’d be the ironic wizard, and I would totally wear a party hat instead of a wizard hat. Why go to the trouble of becoming a wizard if it doesn’t make your life more fun?

@Background Pony #AC7D  
Hey, that’s how they kept hats on back then. https://en.wikipedia.org/wiki/Pointed_hat#Folklore_and_fiction  
There were lots of hats that used a string instead of using “trying to find a just tight enough hat brim and hoping”. There was a lot of windy places. Not to mention ships and horse travel in column formations. If you lose your hat, you can’t go back and get it, or get another one. As a matter of fact, don’t those curved-on-one-side bushman hats have a string? No one mocks those, because they’re popular in Australia, the Army Rangers, and military snipers.  
But wizards? People show no respect for wizards. It’s enough to want to turn people into a frog.

@Dustcan  
well, he’s unironically wearing a party hat with an eye on it on his head.
 
It doesn’t have a brow or anything like a proper wizard hat and has a telltale party hat string around the chin to keep it on like a 5 year olds cap.

This was dumb even for Wizard standards.

Wizards: No sense of right and wrong.

Wizards. The smartest dumb people on the planet? Or the dumbest smart people?