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Now the good news is that you should not have to buy any new kit, with a few alterations your normal 1640s kit should do you. However if you really want to invest in some new kit there are a few extra items you could use. So starting from the ground up:
Footwear. On board ship most of the crew would have gone barefoot for a better grip on the wooden decks and rigging, but we do not recommend that you walk around Whitehaven docks barefoot. Onshore all of them would have worn footwear of some type, Most kinds of 17th century footwear will do latchets, soldiers shoes or bucket top boots, but not start-ups. These were a "land lubber's" style worn by English agricultural workers and were not at all common on board ship or in the caribbean. "Home-made" light leather sandals were very common especially Spanish style Espadrills or even highland brouges would do at a pinch.Hose or stockings are the normal 17th century pattern but because of the heat often made from a lighter material than those worn in Europe, if thick woollen ones were worn they were often rolled down. Or if you feel up to it wear you shoes on bare feet. Hose with horizontal stripes in two colours were very popular with seamen at this period.
Legwear. Standard 1640s breeches are fine, but if you want to invest in new kit there are alternatives. Long wide bottomed canvass trousers. Baggy petticoat breeches like long shorts, often made in striped cotton, with vertical stripes in either white-red, white-brown or white-blue. Or a seamans skirt, a knee length canvass skirt often worn by sailors as it sheds water better than breeches.
Coats, jackets ect: the 1640s style short hip length coats were still common in the 1660s-70s, so a soldiers coat will do fine if that is all you have, any colour will do but blue was the traditional colour for sailors clothing. As we don't want to look too "uniform", if you have another style of coat please use it. A longer late 17th century style with turned back cuffs and pocket flaps is ideal. Or as an alternative just wear a waistcoat without a jacket, both the short waist length 1640s style or the longer late 17th century style will fit this period. Or in the heat of the Caribbean many pirates would have just worn a shirt. Again because of the heat many men would have gone without a shirt and would have worn a jacket over a bare torso. Coats decorated with lace are excellent but slashed clothing is a little "old fashioned" for the late 17th century. If you want to invest in new kit for this period you could get a sailors canvass jacket made up, this is a similar style to a soldiers coat but shorter and with buttoned cuffs to allow the sleeves to be rolled up, they were usually blue and often waxed. Or if you fancy something a little more exotic, many early Buccaneers wore red indian style buckskin hunting shirts.
Headgear. No blue bonnets! At least 10% of pirates were Scottish, but I have never come across any references or illustrations of anybody wearing a Scots bonnet in the Caribbean, (OK, I can think of one, but as it was painted in the Victorian era it don't count). The most common form of hat worn in the Caribbean seems to have been the felt hat, sometimes with white or yellow tape sewn around the brim, and often pinned up at one side or in the front, (sorry but tricornes were very rare at this period). Hats were often decorated with brightly coloured hat bands and feathers, from tropical birds. An alternative form of hat is the sailors knitted woollen cap, this came in two forms, one just like a monmouth cap, the other very similar but having a long tail hanging down the side just like an old fashioned night cap. Another option is to have no hat just a neckerchief tied around the head, often this would be worn underneath a felt hat.

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