Thanks to Hollywood and artists such as Howard Pyle and N.C. Wyeth we have a very distorted view today of how pirates dressed. If we believed everything the movies showed us then all pirates wore big hats, baggy shirts, long leather boots, waist sashes and large coats with enormous cuffs. This image has been applied to pirates in movies set in the mid seventeenth century through to the nineteenth.
The truth is very different. It is doubtful that many pirates ever looked like the ones we see on the screen, but even those that did look like that belong to a very specific time-frame. It is also very unlikely that there was ever much of a “pirate fashion”, making pirates stand out by their appearance. We know that bank robbers don’t really wear striped shirts and masks, or carry bags marked “swag”. That is an illusion, created by popular media to make it easy for we, the consumer, to recognize when someone is a robber. Similarly, the image of the pirate we have come to accept is largely a modern creation.
On the whole pirates probably looked like any other sailors of their period. During Blackbeard's last fight with Lieutenant Maynard of the Royal Navy it is reported that one of Maynard's Royal Navy sailors was shot by another Royal Navy seaman who mistook him for a pirate. The Royal Navy at this time did not have a uniform, and this incident shows us that it was impossible to tell pirates apart from any other sailors by their clothing.
Most pirates were experienced as seamen before they became pirates, many having sailed on merchant, privateer and Navy ships before signing articles. The clothes they wore on their previous ships were designed for their practicality and comfort at sea in all weathers so it seems sensible that they should have carried on wearing them.
It is true that there are records of pirates taking clothing from ships that they plundered, but that probably doesn't mean that they were all decked out in fine clothes of silk and satin. Most of the clothes they stole were probably the same kinds of things as they were wearing themselves, typical seaman's clothing. Occasionally they might have got lucky and plundered a chest belonging to a wealthy merchant, but such incidents were rare.
We must also come to terms with the fact that piracy has been going on a long time, with greater numbers of pirates operating at different periods in history. The popular image of long coat and three cornered hat is certainly based on the general fashions of the early 18th century – the time of Bart Roberts and Blackbeard – but it can hardly be applied to other periods. Henry Morgan would have been confused by a three cornered hat in the 1670s, Francis Drake would not have recognized an eighteenth century coat in the 1570s, and Jean Lafitte would probably have laughed at big cuffs in 1814.
So, to understand the kind of clothing worn by pirates it's important to look at the kinds of clothing worn by seamen generally, and we are fortunate that a number of written records have survived, as well as quite a few pictures from the period.