From Bulbapedia, the community-driven Pokémon encyclopedia.
Ashley (Japanese: サトコ Satoko) is the name given to Ash when he is crossdressing.
Ash dressed up as Ashley in Pokémon Scent-sation! when he was barred access to the Celadon Gym for insulting the perfume which the Gym was known for manufacturing. Jessie, James and Meowth saw that he had been thrown out, and offered to help him get in the Gym with a disguise. He reluctantly agreed, and they dressed him up as a girl. They entered disguised as a family, with Ash playing the part of the daughter, Ashley. He remained incognito for a while, even as Brock and Misty greeted him, but his cover was blown when Pikachu recognized him. Ash tried to ignore Pikachu, but after it hit Ash with a Thunderbolt, his wig disintegrated and his identity was revealed, much to a very angry Erika's dismay. Ash would eventually get his Gym battle with Erika anyway, without the dress.
- Since the incident, Ash has crossdressed again in Love at First Flight. However, this was to roleplay as Juliet for Romeo to practice speaking to. He also crossdressed in Tanks for the Memories! to help out at the Café Cabin. He did it once again in Beauties Battling for Pride and Prestige! (also under the name Ashley サトミ Satomi in the Japanese version), to get into a place that only girls were allowed in.
- Ashley is somewhat significant as evidence that Ash is one of the only characters who can dress up as a female and not be noticed by Brock as a fake. This makes more sense in light of the fact that the Ashley disguise was of a young girl, not the sort of mature woman that Brock would normally be unconditionally attracted to.
- One of Leaf's default names in the Japanese version of Pokémon FireRed and LeafGreen and Kris's in Pokémon Crystal is Satoko, Ashley's Japanese name. The English equivalent, however, is "Jodi." This default name was used again for Dawn and Lyra but its English equivalent is "Britney".