The pork pie hat, made famous by Charles Mingus in his jazz standard “Goodbye Pork Pie Hat”, is another version of the men’s hat variety; often misnamed, it is best described as having a brim and a round crown. The pork pie is historically associated with jazz musicians. Lester Young’s pork pie had a large brim, unusual for a pork pie. This is probably the hat that Mingus referred to in his song.
A traditional pork pie looks like this (worn by Thelonious Monk, weird and wonderful composer and piano player):
Gene Hackman wore a pork pie in one of his most famous roles, but the hat is associated with musicians and beatniks.
A round brim, cylindrical crown and circular middle, the pork pie has no “pinch”. The brim can be worn up or down, but seems most often to be worn up, making the brim look like an upturned plate.
What to wear with it? The pork pie is casual, as Stallone shows in the original Rocky. What to wear with it? As Monk and Lester Young showed, you can wear it with a suit, but only in casual settings (jazz bars?). Wear it to the gym while you are waiting to go a few rounds with the pro, playing golf or making deliveries. A great, low maintenance, all-purpose hat, proving that hats do not have to be formal.