I don't know where Pork Pie got it's name, but after a little research found they resemble food - an English Pork Pie to be exact.  However it happened The Belmont and it's stindgy brimmed bro' The Toledo are a must for certain folks and both of these pork pies are proud to be part of our 'Classic Brims' section for they are just that.  So much so that a song in remebrance of Lester Young was named "Goodbye Pork Pie Hat."  Charles Mingus recorded it in 1959.  Joni Mitchel went on to pen lyrics to the piece.  (Thanks Wikipedia for the dates, etc.)  

So, who looks good in this hat?  Oddly enough I've found folks with round faces look great in them, especially with the brim up which is how the have historically been worn by musicians - but then came Sinatra.  He wore the brim down and that's because of his thin face.  The brim down option is New York business man, 1950's with a thin tie going to his job on Madison Avenue . . . that's the Belmont.  

The stingy brim Toledo goes with tattoos, with thin everything - it's a young appeal and popular with women - the young at heart kind who put it on with some black tights and long shirt and cock it to the side all flirty and cute . . . or straight down close to the eyebrows.  The serious, "You're going to be mine" look.