A lot of people seem under the impression Louis cross-dresses. With the exception of his heels, Louis wears men's clothing, albeit a little "sexed" up. Makeup, too, was common during the Baroque era for both men and women, especially among nobility. He doesn't entertain thoughts of dressing like women at all.
... So James wasn't so abject to swapping outfits on account of he's still wearing men's clothing, albeit just a little frillier than he'd like. Louis dressed as James just looks like he took a step back to one of his earliest designs.
well, considering he is a serial flirt, and we see him shirtless once or twice, why not a Latino chick with big statement jewellery, makeup and tight mufti clothes like she goes out clubbing on a regular basis?
Being that Louis is a pirate and french his clothing would change only slightly I think. He may come out looking more or similar to his sister. James...I don't think they had female officers back then in the royal navy. Regardless it's hard to say what James would look like. But I do love the idea of a gender-bender, would be quite interesting to say the least.
This is probably old and this comment has probably already been made, but, high heels were originally used by MALE aristocrats, them being a female thing is only a later century thing, so, technically, ALL his clothes are masculine! (I sense I spelt something wrong somewhere there...)
He has a stick up his butt<sub>