This is the hat that everyone thinks about when they see gangsters. However, in 1920's Kansas City it was the hat of the middle class worker. Men downtown tended to wear Fedoras as part of their daily dress:
(also note the lower class workers in their preferred flat caps [nowadays called newsboy caps])
Fedoras have a large flat brim and a domed, bowler-like crown that is often folded, pinched, and shaped. The common crown is folded in half front-to-back and then has two circular pinches on the front half. The front brim can also be tilted downward and the back tilted up in the traditional "Noir Private Investigator" or "Indiana Jones" configuration. However, in the 20's hats were bought as blanks (they didn't come standard with the crease already set until the 50's), and men either shaped the hat themselves or had their haberdasher shape it according to their preference, so you can find pictures of fedoras with no fold or no pinches:
(note the two men just left of center, their fedoras have a very shallow fold and no pinches)
I'm not certain, though, that variations were popular in Kansas City. In the above photo the man holding the newspaper on the left is comedian Ben Birney on a visit to Kansas City. The man on the right holding the newspaper is Mayor Bryce Smith, wearing a Fedora more like we see in other Kansas City photographs. However, the biggest Fedora wearer we are concerned with is Tom Pendergrast and his gang of friends:
Tom loved his Fedoras. The fashion also spread to his close friends, as can be seen in the second picture. These make it pretty clear that if you're looking to accurately portray a member of the Pendergrast's business network you want to get an accurate Fedora. Here are some great modern ones:
And some not so good ones:
Although this hat is marketed as a Fedora, the brim is too small and the turn up in the back is too sharp.
This kind of hat could be problematic. I couldn't find any Fedora pictures from the 20's that had the folded crown shaped with an upward curve like this. For example take this picture of the top of Truman's hat:
The crown is obviously folded, not shaped. I think the heavily shaped crown is a more modern variation, but I can't prove it right now, so use caution.
Very similar to a Fedora, a Homburg has a brim that curls up all around instead of lying flat. It's crown can also have the shape variations that a Fedora has, so the curling brim is really the big marker. If the Fedora is the hat of the businessman, then the Homburg is the hat of the politician. President Truman loved his Homburgs. He started wearing them during his local political career in Kansas City in the 20's, and continued through his Presidency in the 50's:
Also, in the crown example picture above his hat is a Homburg, not a Fedora. Note how the crowns are shaped the same.
So, if you want to portray a political crony in Kansas City the Homburg would be the hat of choice. It's actually pretty easy to find Homburgs in modern hat shops. Usually, though, they're listed as Fedoras, so shop around. Here are some modern examples:
I've found a few examples of PorkPie hats as well. The Porkpie is a boater-like hat with a Fedora-like or Homburg-like brim and a short, 3-4" crown with a flat top. When worn, the shortness of the crown means that the flat top can take on a slightly domed shape as the top of the head pushes it upwards. I'm not sure where to place it in Kansas City's societies, though.
Truman wearing a PorkPie.
The man on the far left standing next to Tom Pendergrast is holding a PorkPie.
A young man in this Kansas City crime scene photo is wearing a PorkPie. It is hard to tell, though, if he is an investigator or a criminal, or just an innocent worker in the business.
There are also some more famous people from the 10's, 20's, and 30's who wore PorkPies:
Buster Keaton's PorkPie is famous and a hallmark of his silent film characters. Some PorkPie wearers could be looking to emulate film stars such as Keaton.
Lester Young loved his PorkPie so much he wrote a song about it in the 50's. Like Young, many Jazz musicians embraced the PorkPie, and it also became a signifier for Jazz music and culture.
There is one other person famous for wearing a PorkPie, even though it is after the time period at hand. Robert Oppenheimer, an American scientist known as the father of the Atomic Bomb, was also a dedicated PorkPie wearer:
The good news, though, is that there are a variety of hats for men to wear at KC in 2016 bid parties. I hope to see lots of hats at cons in the coming years!