You mean to say that they are not _all_ already female smileys? Well, except for the Rackham flag, anyhow...
How would one tell, at any rate, being a featureless little smiling head, as to its sex? [No jokes about sex and smiling heads, thanks.]
As to the discussion of Female Pirates, there's been lots of suggestions for good sources. Remember, Anne and Mary are well known because they make for good story, with an amusing end to the tale. Most "real life" pirates don't go down in infamy for generations, male or female, black or green.
- Calico Jack