People are very easy to jump to “Ashley” of the first or second season, in which Ash cross dressed to be in some sort of contest against Misty. Here’s my take on it:
There are many possibilities to what Ash would be like, but only a few probabilities.
Ash(ton) the tomboy
No major difference in personality. The only considered appearance changes would be longer hair - in the back, and skinny pants. I see some slight differences such as Ash being more excitable. In story arc Ash may have to face gender discrimination (and over come it, because she’s the main char), and somewhere in there be exposed to her friends as a girl (if not from the start). Maybe slightly longer hair to keep it in mind to us or the show Ash is female.
Non - gender complex:
It would help if Ash refereed to herself in gender neutral terms. Others would take it upon themselves to call her male terms, and she wouldn’t correct them. She would put on a shirt and swim trunks instead of a bikini style swimsuit. The gender reveal would most likely be comedic. She would be changing or something and someone would be in and be “OMG! *manic blush* You’re a girl?!” and she would just grin, and like “Yeah. You couldn’t tell?” “Why did you let us think you were a boy?” “It doesn’t matter, to me.” After that things would be awkward for alil bit, but funny awkward to us. I would see Misty’s role changing for whatever she was suppose to be to maybe trying to Ash fem up, and/or open any homosexuality. Brock would keep his role as the mature motivator to Ash, but add trying to get her to be more fem, and/ or open any heterosexuality. There’s also the chance Brock might treat Ash like the boy he’s been leading everyone on the believe, like with playing “bro” games. Ash’s sexuality may be expressed as bi, pan, or ace, in reality.
Gender complex, in reference to female:
Ash would look like a boy, but get uptight would people say anything in male terms about her. No funny gender reveal. Despite her looking and acting like a boy, she’d keep it clear she’s a girl. She would be more likely to pick heterosexuality, to overdo keeping in mind she’s a girl despite her real sexuality, if not hetero.
Gender complex, in reference to male:
She would refer to herself in male terms, and so would others. The gender reveal would be a serious character development stepping stone, instead of funny. It could go as Ash hating being a girl, and be an issue to over come to accept being a girl. It could be Ash was posing as a boy for a reason, but being ok with being a girl. After the gender reveal her outfit would most likely change to a more fem version of what she’s already wearing. The attitude would still be very much the same, except she would just refer to herself as female from there on out.
Ash(ley) the fem girl.
I highly doubt Ashley would anything like “Ashley,” the first Ash cross dress. To go into my full idea of a feminine version of Ash’s outfit is, based on how Pokemon does things: A longer jacket, short shorts, choker, knee or thing socks (given socks are worn), and a tank top. All in a lighter color scheme. But that’s my idea of Ashley being maintained in the original male Ash look. The real Pokemon Ashley might look COMPLETELY different from the male counter-part.
Goes for both: I’m thinking Brock being the way he is might be inappropriate, but that would be given if he found Ash attractive.
Those are all my theories. Now here are some facts:
In Ash’s anatomy, the story starts with Ash at 8, I believe. At 8 years old, back in the 90s, girls didn’t have boobs. Ash won’t look any more boy-ish or girl-ish in a plain shirt and shorts. All children can start traveling alone at a young age. I don’t remember any rules about boys and girls starting at separate ages. Ash would start her journey asap, like the original. The crossing dressing “Ashley” wouldn’t have happened, but that doesn’t mean cross dressing wouldn’t happen at Ash at all. Instead of putting on a dress for Misty, she would have put on a different male outfit for Brock. Changed Ashley to Ashton, Ashton to something else, or be only known as Ash until Ashton would have been needed. Overall, not that much would be different. Just whatever you need for gender reveal, tom boy accommodations, or make the character fem.
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