Ash dressed up as Ashley 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. As Ashley, Ash wore an orange frilly dress that had a pink ribbon in the back, a blonde wig with a pink ribbon and red high heels. They entered disguised as a family, with Ash playing the part of the daughter. 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 he was hit 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. Ash reused the name Ashley in Beauties Battling for Pride and Prestige!.
- Since the incident, Ash has cross-dressed again in Love at First Flight, Tanks for the Memories!, Beauties Battling for Pride and Prestige!, and Real Life...Inquire Within!.
- One of Leaf's default names in the Japanese version of Pokémon FireRed and LeafGreen, as well as one of 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".
|Japanese||サトコ Satoko||From Satoshi, Ash's Japanese name|
| English, Danish, Dutch
Finnish, German, Italian
Portuguese, Spanish, Swedish
|French||Natacha||From Sacha, Ash's French name|