I know of at least two songs that talk about a girl having a 'pirate smile.' unfortunately, I think the reference is lost on me. I have no idea what a 'pirate smile' looks like.
Was it a pop culture reference of the time that just went out of fashion, like 'bette davis eyes?'
When I googled it, all I found were lyrics for songs, blogs, smileys wearing eye patches, and other equally useless items.