A bit late but if ye be interested for future ventures I can point ye to some references to answer some questions and notions mentioned within the first few posts of this thread.

Since taking me leave of the Poser communities I have been running with pirate reenactor groups of the GAoP (Golden Age of Piracy). We do Ren faire and Pirate festivals doing black powder demonstrations, mock sword fights, and much chasing o' wenches and drinking o' rum.

As for the "period" o' what ye speak; first I noticed you mentioned Tortuga, therefore I would assume ye be speaking of the GAoP wich falls between 1650 and 1730 (give or take 20 years depending on who you speak to).

As for the types of material; unless ye be from the Orients then mostly ye be working with fine linens, wools, and leather also hemp (a few others as well but I not be a tailor). Cotton would be rare as it was hard to come by and very pricy, not much of it to be found with the English, French, and Spaniards that roamed the Caribbean...some, much not much.

Ok, I like P3D's outfits too myself, but in reality the dresses of the period where longer...MUCH longer.
s296.photobucket.com/albums/mm173/Mad_L_photos/Pyrates/ (a few of my own P3D renders)
Actually the only couple female pirates known dressed as men, pretending to be men actually; aye, I be speaking of Ann Bonny and Mary Reed.
Now earlier in history there was one other, known as "The mother of pirates", an Irish lass; Grace O’Malley. Now she wore dresses as best we can tell, but they also where long dresses, down to her ankles.
Now there were a few other female pirates recorded in the logs of history, but I have seen no others that offer any paintings or even period artist interpritations of how they dresses, but by descriptions given it would be safe to assume they either wore traditional long dresses or dressed as a man.

Now, on to the boots; a much debated subject in the priate world. There are still some who insist that "pirates Never wore boots" - BUT, that has indeed recently been debunked! For the pirate ship the Whydah has been found to have boots aboard, but currently only shoes are on display. Also, we have recieved recent word that there have been found an entire cobbler's shop in the now under water remains of Tortuga itself, it is said to have entire shelves of "boots". So far no renderings or artifacts have been made public as this word was just revieled last year in a forum by one of the researchers working there...he says details will come later as this finding was not what they were actually after so it is 'on the back burner' at this time - BUT, these two findings do show that while it was uncommon, pirates DID have access to boots. While no further information at this time has been given, we are assuming they are most likely Musketeer-like in fashion. However, a woman's boot would be much shorter, women of the period seldom had boots reaching half way to the knee, again because they NEVER wore short dresses. Even those who did dawn breeches or even pantaloons would have boots that only reached within an inch or two below the knee.

As for the Bucket, or Muskateer type boots, a good resource would be Loyalist Arms who has a cobbler which has been making us exact replicas of both Muskateer boots as well as just last year he his now making us Exact replicas of the shoes recovered from the pirate ship Whydah:
www.loyalistarms.freeservers.com/clothing.htm

Shoes and boots of the period where Leather, all leather, leather souls, in some cases such as these shoes and boots they have full pegged wooden heels.
And trust me, we have experimented and I can vouch first hand that neither would be of common wear while on board a ship - wet leather is SLIPPERY! Actually most will agree that pirates, while on ship at least, went either bare foot or some have been painted to wear sandals made of hemp rope (the likes of what many of us would like to find a good maker of...oh yes, there are a couple out there, but they are not of proper making and so far none of us have been able to convince the makers to accomodate us...it took two years to convince Loyalist to make proper shoes so pirate reenactors could stop wearing civil war and coloniel era designes)

Now if ye wants a bit more Hollywood style in yer boots then ye can take a look at the ones actually made for POTC movie, the very place mine own come from, CAboots. Here be examples of Will Turner, Jack Sparrow, as well as Barbosa and others:
www.caboots.com/category/mp/

On to the part about weapons; again Loyalist would be a good start, after all they supplied many of the black powder firearms for the Disney movie POTC:
www.loyalistarms.freeservers.com/pirategoods.htm

Now if ye wants a bit more true-t'-life information t' work int' yer renderings then ye may want t' take a look at some of the hard core reenactors of piracy, for that I would recommend browsing the pages of Gentlemen of Fortune, there they deal with realistic sailors of the GAoP era and have a full detailed description of the 'common sailor' who would be pirate and what his clothes would be and type of gear he would have access to:
www.gentlemenoffortune.com/

For some fantastic examples of swords, some period, some 'artisticly enhanced', I would recommend a visit to Baltimore Knife & Sword, maker o' some o' th' finest in REAL and STAGE swords there be:
baltimoreknife.com/
and for some more hand forged, and truely period, sword that will set ye t' drewl'n in yer rum then take at look at Old Dominion Forge:
www.olddominionforge.com/swords.html (swords)
www.olddominionforge.com/knives.html (knives)

Other links for information, inspiration, and links t' even more information:
www.noquartergiven.net/ (pirate news magazine, browse site for tons o' links t' tons o' resources)
www.bilgemunky.com/ (Bilge Munky pirate radio as well as he's reviews on all things 'pirate'..including RUM)

And if ye do not wish t' be gutted 'n yer inards fed t' the fishes then also stop by 'n visit th' True pirate wench, one one and only, the Doxie with Moxie, Scarlett Harlott:
www.scarlettharlott.com/index.php (but of course she tis Not a 'period' pirate wench, but she sure be Inspirational!)