Pokemon Fantastic! Team Rocket Fantastic! James, as the male half of Team Rocket, carries the burden of representing the ethics and hard-edged ruggedness of the criminal organisation. That is why he has has a poncy voice and often dresses up like a girl!

Ofcourse, he only dresses in skirts and wears wigs because it is in Team Rocket's interests... James along with his partner Jesse are on a mission to capture Pikachu... only they keep screwing up!! oh no!!!
The dressing up is part of fooling their enemies so that they can steal pokemon, but James always gets discovered... with hilarious consequences!!!

It is always fantastic news when James cross dresses!!
Check these episodes:
Battle Aboard the St.Anne
Pokemon Fasion Flash
The Misty Mermaid
In The Pink



If James is not a big poof, then why does he take every opportunity to dress like a woman. At one point he even pretends to get married... but he plays the bride and Jesse plays the groom... Oh them!