Pork pie hat
A pork pie hat is one of three or four different styles of hat that have been popular in one context or another since the mid-19th century, all of which bear superficial resemblance to a culinary pork pie dish.
The first hat to be called a pork pie was a hat worn primarily by American and English women beginning around 1830 and lasting through the American Civil War. It consisted of a small round hat with a narrow curled-up brim, a low flat or slightly domed crown with a crease running around the inside top edge, and usually with a ribbon or hatband fastened around the shoulder where the crown joined the brim. It was often worn with a small feather or two attached to a bow on one side of the hat. Such hats might be made of any number of materials (straw, felt, cotton canvas covered in silk, etc.)—what made them "pork pies" was the shape and crease of the crown and the narrowness of the brim (sometimes called a "stingy brim" in reference to its brevity).
Buster Keaton and the 1920s
The pork pie began to appear in Britain as a man's hat not long after the turn of the century in the fashion style of the man-about-town, but its resurgence in the United States in the 1920s is credited to the silent film actor Buster Keaton who wore them in many of his films. The hats from his films were ones the actor made himself by converting fedoras and other hats into pork pies, creating more than a thousand in his lifetime. This kind of pork pie had a very flat top and similar short flat brim. 
1930s and 1940s
Arguably the heyday of the pork pie hat occurred during the Great Depression. In this incarnation, the pork pie regained its snap brim and increased slightly in height. The dished crown of such hats became known among milliners as "telescopic crowns" or "tight telescopes" because when worn the top could be made to pop up slightly. Furthermore, as stated in a newspaper clipping from the mid-1930s: "The true pork pie hat is so made that it cannot be worn successfully except when telescoped." The same clipping refers to the hat also as "the bi crowned". Among famous wearers of the pork pie during this era are Frank Lloyd Wright, whose pork pie hat had a very wide brim and rather tall crown. Lester Young, whose career as a jazz saxophonist spans from the mid 1920s to the late 1950s, regularly wore a pork pie hat during his performances, and after his death the composer Charles Mingus wrote an elegy for him titled "Goodbye Pork Pie Hat". Young's pork pie had a broader brim than seen in earlier styles but retained the definitive round, flat, creased crown.
After the end of World War II the pork pie's broad popularity declined somewhat, though as a result of the zoot suit connection it continued its association with African American music culture, particularly jazz, blues, and ska. In television between 1951 and 1955, Art Carney frequently wore one in his characterization of Ed Norton in The Honeymooners, and in Puerto Rico the actor Joaquín Monserrat, known as Pacheco, was the host of many children's 1950s TV shows and was known for his straw pork pie hat and bow tie—in this incarnation, the pork pie returned to its Buster Keaton style with rigidly flat brim and extremely low flat crown.
The porkpie hat enjoyed a slight resurgence in exposure and popularity after Gene Hackman's character Jimmy "Popeye" Doyle wore one in the 1971 film The French Connection. Doyle was based on real-life policeman Eddie Egan, who played the captain in the film, and his exploits. Egan was famous all his life for wearing a pork pie hat, and refused to surrender his hat to Gene Hackman to wear in the film. The producers were forced to obtain Hackman's hat elsewhere. At about the same time, Robert De Niro wore a pork pie hat in the 1973 film Mean Streets (the same hat he wore when he auditioned for the film).
Today the wearing of a pork pie hat retains some of its 1930s and 40s associations. Fashion writer Glenn O'Brien says, "the porkpie hat is the mark of the determined hipster, the kind of cat you might see hanging around a jazz club or a pool hall, maybe wearing a button-front leather jacket and pointy shoes. It's a Tom Waits, Johnny Thunders kind of hat. It has a narrower brim than a Fedora and a flat top with a circular indent. Usually the brim is worn up. It is often worn with a goatee, soul patch, and/or toothpick." Bryan Cranston's character Walter White wears a pork pie hat in the AMC series Breaking Bad when he appears as his alter ego "Heisenberg" whose persona is associated with the hat.
The military pork pie
"Pork pie" is also used in reference to brimless hats worn by sailors of the United States, the United Kingdom and other nations. This hat is typically round, flat on top and wider at the crown. This type of hat is also known as a "square rig".
American enlisted sailors' white porkpie style hat is referred to as a "dixie cup".
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- Pork Pie Hat vs. Fedora—Article on key differences in hat styles