I Just Ninja'd Your Pirate...
...And I think she liked it.
Jumping in head first here, one of the first things I'm bringing to the table is the posing. It is pretty dynamic and I think it works out much better than having her simply standing there. It seems a little off balance, but then again I cannot see the legs and they blend in to the background a lot, so that makes it much more difficult to tell.
I think you have done a pretty good job on the costume over all. You added good dynamic wrinkles to the cloth, which helps continue the continuity of the piece. You have also done well with making the cloth react well to the body and the rest of the gear. One place in particular is the pistol. I love how you took the time to make the cloth look like it actually going around the pistol, not just simply flat.
Moving from the good to the bad...
The lighting in this is kind of hard to swallow. The lack of highlights kind of hurt, but I'm not going to dig too deep on that since I neglected it on another recent project of my own. The hard black you have is a little rough. In some areas it is blending straight in to the background. This makes it hard to see the actual mass of the character and makes it seem weird.
The silhouette in the background is a little off setting, and I personally don't like it. But it does help see the edge of the shoulder.
I feel the proportions are a little weird, but this is in part to the shadows . Again, not being able to see the whole thing can be a little throwing.
This is more of a moot point but I just gotta say, gimpy kunai? lol he pistol looks good though.
As for things I would change...
I think you should have gone ahead and made the goggle lenses opaque and then had some real fun with some highlights and some reflectivity.
lol I do think Bob will be pretty happy about it over all, and it will make a swell gift. you'd probably get more views though if you kept the Icon on the boobs though :P