If ye be just startin' out aquiring an outfit, a grand Pirate Shirt could be the first item of pirate clothing.
Ye need ta figure out if you will be a fancy Gentlemen of Fortune (then get the gentlemen shirt or a colonial shirt) o' a rugged Buccaneer (then get the sea worthy or sea rover shirt).
If ye be needing a 15-16th century shirt, then go fer the Buccaneer Shirt.
I have been wearing the same Rogue Shirt Pirate fer three years, almost everyday, they are high quality and will serve ye well. We now have pirate shirt in many different colors n sizes to fit anyone from XS to XXXL.