Some of the most famous pirates were Caribbean buccaneers of the 17th century. The buccaneers began as hunters on the island of Haiti, but throughout the 17th century spread across the Caribbean, preying on Spanish settlements and shipping. Because of their roots as hunters, in many cases their clothing was completely different to that of other pirates.
This picture of a hunter-buccaneer is based on several different pictures of the time. The most striking difference between this man's costume and that of other pirates is the long shirt he is wearing. This appears to be a kind of heavy over-shirt or smock, worn for hunting, and is very similar to the hunting shirts popular in the late 18th century amongst backwoodsmen. It is tied at the waist with a belt, cord or narrow sash to prevent it being too loose and to lift the hem up to give freedom of movement to his legs.
He is not wearing breeches of any kind and that again compares well with other pictures of buccaneers such as one dating from 1700, and showing French buccaneers of that time. This indicates very strongly that the men in both pictures are quite definitely in working clothes for hunting and warfare, not fashionable outfits for wearing about town. Another peculiarity about the clothes worn by these hunter-buccaneers is that instead of stockings many of them seem to have worn long lengths of fabric wound round and round their lower legs like puttees, and some are shown barefoot.
In some respects the hunter-buccaneers did wear similar clothes to other pirates and seamen. Several of the buccaneers shown in period engravings are wearing short coats like seamen, for example. The headgear favoured by the hunter-buccaneers of the West Indies was a simple cap, with a small peak at the front.
All in all, the clothing worn by the hunter-buccaneers was designed with nothing but practicality in mind. In the sweating jungles of Haiti and Panama heavy woollen breeches would have been intolerably hot and uncomfortable. Long coats or waistcoats would have been equally hot, and would have been impractical for cutting through dense undergrowth. The men who had spent their lives in the backwoods of the West Indies certainly knew what they were doing.
Not all buccaneers were hunters however, many were just soldiers and seamen who traveled from Europe to wage war against Spain in the New World. The picture above for example shows a buccaneer dressed typically as a seaman from the time. He wears baggy breeches, a short jacket or waistcoat with "mariner's cuffs" and a baggy cap, and is probably typical of the many thousands of men who made their names with Henry Morgan and Francois L'Ollonais.
The clothes worn by the seaman in the picture are based on a list of clothes specified as being sold to seamen of the Royal Navy in 1663. An earlier list of clothes sent out with the Navy ships which captured Jamaica from the Spanish in 1655 might also be of interest:
Canvas drawers [in this case drawers probably refers to breeches rather than underwear]
Rugs [this probably refers to overcoats]
A good number of buccaneers were neither hunters nor seamen, but men who traveled to the West Indies first as soldiers on one of the many military expeditions sent there in the seventeenth century. The first significant expedition send out by the English was that of 1655 mentioned above. The men who made up that expedition were drawn from the dregs of the English army, and received little in the way of equipment – certainly nothing more suited to tropical conditions than their normal uniforms. They probably retained their red coats, grey breeches, and knitted caps. Perhaps once they arrived in the Caribbean they modified their uniforms, but if they did there is little record to show it.