"I was assigned a gender. The only thing I was born as was an absolute legend!" Has to be the best quote I've ever read.

Thanks, I was pretty proud of that line

As you should be

um, I remember the tradition of men wearing skirts (To be exact,kilt) in Scotland... And I think what kind of clothes a person is willing to wear is not because of himself, but because of social stereotypes.

P.S.
that story is well written, but I think there are few elements related to pokemon... Do you really not consider the ideas I provided before? 😭😭 (that Heart Swap thing)

Yes, there are plenty of examples of men traditionally wearing skirts. And yes, the clothes a person is willing to wear is mostly just social stereotypes. James is just embarrassed and scared of going against social stereotypes. He wants to do things the way he's 'supposed to'. Fortunately, Sammy is helping James break that mindset.

Yes, there aren't any elements related to pokemon; this idea worked better with humans (it'd be hard for a Mudkip to wear a dress lol), so I made them humans for this story. I've actually started writing the Heart Swap story, and I really like how it's coming along! I just got distracted by other ideas lol

Indeed, it is difficult for a quadruped to put on a dress, but there are many ways to solve this problem. For example, you can let Jamie "evolve" into a marshomp, or default the pokemon in this story are anthropomorphic. At least there's simpler solution is bypass the dress and replace it with other feminine dress-ups, such as bow, the head clothes wear by women or arrange flowers on head.

I could do that, but since this story idea has nothing to do with pokemon, it's simplest to just make them humans. I only needed their personalities for this story.

I guess you could imagine them as anthropomorphic pokemon; nothing in the story explicitly calls them human.

Probably the magic. The laws of nature are very strict about clothing!