Pirate Hats

There's certainly an element of truth in these images, however that are greatly exaggerated by stories and, in particular, Hollywood movies.
Pirates almost always wore some form of headgear. This was a practical necessity rather than a fashion statement - working all day on one of the old ships would have left them exposed to the sun, which was especially strong in areas such as the Caribbean. Not doing something to protect against this would have been foolhardy.
What Did Pirates Wear?
The Tricorne
The traditional tricorne was an authentic part of the naval uniform of some countries, however it's unlikely to have beeen worn at sea by the average working pirate. Pirates were pragmatic people and an exotic uniform simply wasn't practical on board ship. It would probably only have been the Captain and his most important officers who wore one regularly. Of course things might be different on land - pirates could be as fashion conscious as anyone else and a good hat might be donned before entering port and visiting the local inn. In some ways the tricorne could be thought of as a "dress uniform".Some pirates were more flamboyant than others. It's said of Black Bart that he used to wear "a rich crimson damask waistcoat and breeches, a red feather in his hat, a gold chain round his neck, with a diamond cross hanging to it".
The skull and crossbones image on the front of the hat is unlikely to have been common - there was no "standard" pirate flag, most ships having their own version of the logo.
Headscarf
For most pirates a practical on-ship head protector was the simple scarf tied around the forehead. This was simple, cheap and effective - it also doubled as a sweat band. As with the tricoern, individual pirates would have had thir own preferences regarding simple or ornate designs.
Caps
Somewhere between the tricorn and the head scarf there was the plain cap. This would probably have been a simple knitted affair. One version mentioned in some accounts is known as a thrumm cap.
