Pirate Costumes-8 Bells

Ahoy, mates (look, I'm afraid there might be quite a bit of this nautical language throughout these pirate posts...so bear with me).

Here begins our exploration of pirate costumes for Halloween, a vast subject indeed, so keep a weather eye open and let's turn to, handsomely now.

Jack Sparrow
We might as well start here, with Jack Sparrow.  Due to the overwhelming presence of Johnny Depp and the unexpected success of the POTC franchise, Jack Sparrow has become for the modern audience what Long John Silver was for previous audiences, that is to say, the default celebrity pirate.  As such your Jack Sparrow and Sparrow-inspired options are many including licensed, unlicensed, and knock-off options.

Two true costumes here.  Each of these is a very nice Jack Sparrow option.  They look great, but take warning, many of the items pictured don't come with the costume itself.  You will need accessories, including the footwear and the whole package is likely to set you back a few hundred bucks.  The coat on the left is the more complete picture, but he is wearing the hated BOOT TOPPERS!  The boots on the right are at least a hundred and a half so really your whole outfit could run you $300+.  You don't have to go "official" however. Oh no.  There are options.

Mock Sparrows

These three above are what I call "Mock Sparrows".  With their dreadlock wigs and gypsy looks they invoke the idea of Jack Sparrow without having to actually look like Jack Sparrow.  Ah yes, the unfortunate conflation of gypsies and pirates is perhaps the most damming of all the Sparrow Sins.  Huge hats, scarves, braided beards and all manner of jewelry and "rock star" attire, including eye shadow make these fellows less pirates and more prostitutes.  A is not too bad.  He's far too happy and he has boot toppers that do not match his shoe color in any way.  B is clearly Mia Sara of Legend "cleverly" disguised as a pirate, no doubt to escape the attentions of Matthew Broderick.  Mia has chosen, instead of boot toppers, to wear some sort of puffy false boot, which actually manages to look worse than A's mismatched footwear choice.  I'm not seeing pirate so much as rent boy.  C is very likely comedian and filmmaker Sacha Baron Cohen (look carefully now) and is not a bad costume either.  Remove the sash, the braided beard and the wig and you have a decent coat, waistcoat, frilly shirt pirate.  A little too slick, but hey, not bad.  Of these three C's boot toppers are the least offensive but also the least piratical.

From "lovable" rogues we move to "heroes"

Jack Sparrow began not as the be-all end-all of pirates, but as the roguish mentor to Will Turner.  In Will Turner we had a more traditional pirate film type of hero.  In the pirate films of yore the star was often not so much a pirate as a privateer or adventurer or even a victim of circumstance keeping his heroic code while walking the line of piratical activities.  Men like Henry Morgan and Francis Drake, adventurers and privateers were the model of the pirate heroes of old and this is the style of pirate we see in the picture above (the Fabios).  Simpler in design and attire without the gypsy locks and jewelry, free of the eye shadow and devilish grins.  Yes the guy on the left looks like the pirate you see on countless romance novel covers bearing titles like Her Pirate Passions or The Buccaneer's Wench and his look makes a good gateway to bring us from the Jack Sparrows to the Heroic would-be Will Turners.
The key thing about these three is the simplicity of it all.  Puffy shirts, tight trousers, boots (toppers) and maybe a sash.  These are the heroic types evoking Errol Flynn.  They are decent enough with the right accessories, although they guy on the right is just boring.  He could be the hero in any number of made for SyFy movies set in non-specific time periods or fantasy worlds.
I'd even use that as a basic Inigo Montoya from The Princess Bride in a pinch.

Never fear, mates, they get better...and worse.

Keep yer punkins lit.