One hat per person, please

[Brown_Eyed_Girl]

Newsboy cap. Soon to be known as the Pittboy .

[PaulParkhead]

The bowler hat of an Ulster Orangeman. Well, it’s not a profession, as such, but these guys do take it seriously.

[Apollyon]

NZ Army Lemon Squeezer, very similar (if not the same) as the US drill instructors’ campaign hat

[Mr.Rosewater]

@Booker57

A Chicago cop hat with the checkerboard band.

Please tell me why they have that. thank you.

Hopefully, not too great a hijack

I only have a wiki link, but here is a bit of info on that checkered band.

@Wikipedia

Chicago police wear hats with checkered bands, popularly known as the ‘Sillitoe Tartan’ and named after its originator, Percy J. Sillitoe, Chief Constable of Glasgow, Scotland in the 1930’s. While the checkered band is a common police symbol in the United Kingdom and other countries in Europe, the Chicago Police and the Pittsburgh Police are the only police forces in the United States that have adopted it as part of their police officer uniforms.

[brujaja]

Asshat.

Sorry, couldn’t resist!

Seriously, Princess’s hat.