A Draggletail is just what it appears to be, a tail, especially a skirt tail, that drags, and particularly the person thus dragging her skirt in wet and mud.
And inasmuch as one so careless of appearance is likely to be careless in morals as well, the term has frequently denoted a woman of loose character.
Not always, though, and not always applied to women.
A group of woebegone soldiers, for instance, defeated in battle, anxious for nothing but to save their skins, too tired to maintain any semblance of order, just dragging themselves along, may also be draggletails.
