Tweed Herringbone flat cap
A flat cap is characterised by a soft, round brim in the front. Although it is recommended for casual wear, there are those who go their own way and wear it with formal wear. Although not advisable I have seen some gentlemen making it work. And although the flat cap pictured above is rather chunky, in a heavy herringbone, they are also available in wool and a lot slimmer and sleeker. This cap is also known for its warmth, thus becoming a shield against cold and wet weather.
Stokley Williams wore a newsboy cap, also known as a gatsby or what I like referring it to as; an Eight Panel, in the 'Someone to Love' video. And Shawn Stockman of Boyz II Men fame wore one in the video for 'On Bended Knee', with the button attaching the front to the brim undone. I prefer the name Eight Panel because it is self explanatory; the top of the cap is divided into eight panels which converge at the centre of the cap, held together by a button. This is also a casual cap, which is worn a lot in certain subcultures; hip hop being one of them. Just the other day Raekwon the Chef was wearing an Eight Panel, rather appropriately, on the Monique Show.
What I have found in my research on these caps is that the one cap advocated by most for formal wear is the Ascot cap.
The Ascot cap, although similar to the flat cap, is a hard men's cap distinguishable by its hardness and rounded shape. It is typically made of felt or wool. In two columns I read I found that an ascot cap made in felt is recommended for formal wear because it is modern and blends in with the modern aesthetic of formal wear. With an ascot cap you look a lot less than a farmer in the city and more like a modern man adhering to stylish sensibilities.
Another version of the flat cap I have come across is one with air vents on the sides just above the ears. I doubt it is still in production because the images I have of this cap are "stills" from a popular South African comedy from the early 90s titled 'Velaphi'.
I wouldn't rush to call them air vents because they are a derivative of a certain function. This cap has adjustable side tabs which allow for fitting on different size and shaped heads. The vents come about because the cap is either tightened or loosened according to the wearers preference.
PG: Man to man, generation to generation.