18th Century Love

Well contemporary depictions of Anne Bonny and Mary Read depict them dressing as men as well. Not that they were the only female pirates, and personal reasons for breast-binding aside, men’s clothing was just more practical to wear on the high seas. If ever you were to fall into the water, you’d sink like a stone in a dress, and not every woman was Chevalier D’eon and could sword fight in a dress. But if a woman chose to not wear pants, I imagine it would have to be a loose skirt of plain thin cotton, as any other material would be too heavy, too hot, or ruin easily. Corsets are also out of the question, as completely unrestricted movement of the upper body is required for proper sword fighting. Heeled boots as well would be impractical. You can just imagine a female pirate getting caught in the holes of the wooden planks. Just keep in mind on what would be sensible to wear, and eliminate those that aren’t. So in the end, imagine a female pirate wearing a hat, a tricorn perhaps to keep away the bright sun, boots, pants or loose cotton skirt, a loose shirt, not necessarily breast-bearing, a belt with her chosen weapons, a few tattoos, maybe ones similar to those of conscription, not that she would’ve been forcefully enlisted on any ship, but wants to show her comradery. And then of course there’s nothing wrong with wearing the trinkets claimed during raids and pillages. So you see, it’s not so much cross-dressing but necessity that would call for dressing “like a man.”