I've heard "Cutty Sark" translated as "short skirt." "Short skirt" sounds sexier, and more feminine, than "short shirt", and therefore a better name for a ship, but maybe that's just my bias!

Maybe sark is ambiguous and could mean either shirt or skirt—maybe it's a kind of shift or smock.

Come to think of it, I wonder if all these words—shirt, skirt, shift, sark, and smock—come from the same ancient root. I suppose the design of clothing, and the words we use to describe it, are as variable as music is, and could be considered a branch of folklore unto itself.