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!.
|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|
- In Love at First Flight, Ash wore Juliet's outfit and a wig that looks exactly like her hair to help Romeo talk to her.
- In Tanks for the Memories!, Ash and Pikachu wore a French maid's outfit while helping at the Café Cabin.
- In Beauties Battling for Pride and Prestige!, Ash wore a light blue dress with a light pink bow in the middle, and a pink wig with yellow bows on each side, and Pikachu disguised as a female by sticking a heart-shaped piece of paper on his tail.
- In Real Life...Inquire Within!, Ash wore a nurse outfit similar to the one that the Nurse Joy of Melemele Island wears. At first, he wore the female uniform, but later, he changed to a male uniform.
- In Climbing the Tower of Success!, Cilan and his Pansage dressed like Elesa and her Emolga in the costume contest portion of the Wishing Bell Festival.
- In Beauties Battling for Pride and Prestige!, Cilan wore a pink dress with red roses and a blond wig.
- In Battling at Full Volume!, Serena posed as Ash by wearing his clothing.
- In Battle Aboard the St. Anne, James appeared in ganguro style, infamous for having dark tans and bright makeup. The outfit included black shoes, a short skirt, and a blonde wig that somewhat resembles his regular hairdo, making this the first time that James dressed like a woman in the series.
- James wore a two-piece bikini with giant inflatable breasts in Beauty and the Beach. The swimsuit was never seen in the English dub, since the scene containing them was cut.
- In Abra and the Psychic Showdown, James wore a hula girl outfit complete with a lei necklace, green grass skirt, and wig.
- In Pokémon Fashion Flash, Jessie and James cross-dressed in a fashion similar to that of the manga The Rose of Versailles. They reused these outfits in I Feel Skitty!.
- In The Punchy Pokémon, Jessie, James, and Meowth stole Giant’s clothes and Hitmonlee to enter the P1 Grand Prix, with Jessie being the face of Giant.
- In Who Gets to Keep Togepi?, James posed as a female Egg-seller with an old-fashioned dress, bonnet, and basket full of fake Pokémon Eggs in an attempt to steal the Togepi Egg.
- In The Purr-fect Hero, Jessie and James performed a fake magic act for the schoolchildren, with Jessie wearing a magician's tuxedo, top hat, and glasses, and James wearing a pink dress and disguised as the lovely assistant.
- In The Case of the K-9 Caper, James disguised himself as Officer Jenny. He reused this outfit along with Meowth in Losing Its Lustrous! and Double Team Turnover!.
- In The Misty Mermaid, Jessie and James wore Swan Lake-inspired costumes and performed in the Cerulean Gym's Underwater Ballet show. Jessie dressed as a prince while James was in a pink tutu. James's ballet outfit reappeared in Flower Power.
- In To Master the Onixpected!, Jessie posed as an old hermit with a long beard and attempted to steal meatball kebabs from a rest stop near Mt. Hideaway.
- In All Fired Up!, James disguised himself as a League Official in an ancient Greek maiden's costume
- In Fire and Ice, James disguised himself as an ordinary nurse, with a surgical mask covering his mouth and glasses, at a fake Pokémon Center that he and Jessie had set up.
- In Poké Ball Peril, Jessie disguised herself as a male air captain with a moustache to lure Ash and Misty onto the Team Rocket trio's airship.
- In Wherefore Art Thou Pokémon?, Jessie and James cross-dressed as a newlywed groom and bride, respectively.
- In The Totodile Duel, James posed as an auxiliary lady from the Pokémon Battler's Association.
- In Espeon Not Included, James disguised himself as a Geisha girl while trying to steal an unevolved Eevee that would later evolve into an Espeon.
- In Pros and Con Artists, James and his Cacnea (confirmed male in the English dub only) posed as satisfied female customers at the trio's fake Pokéblock shop in Fallarbor Town as an attempt to scam money from the competing Pokémon Coordinators.
- In A Double Dilemma, Meowth disguised himself as May.
- In Claydol Big and Tall, Meowth dressed as a female cheerleader and Jessie's Wobbuffet dressed as a maiden to attract and quell a rampaging giant Claydol, which proved successful in Wobbuffet's case. Wobbuffet wore this outfit again in Tanks for the Memories! while working as a maid for Team Rocket's pop-up café.
- In Deceit and Assist, having stolen his Contest Pass and Ribbons, Jessie disguised herself as Anthony in an attempt to enter the Hoenn Grand Festival.
- James dressed as Nurse Joy in Like a Meowth to a Flame.
- In Three Jynx and a Baby!, Meowth disguised himself as a Smoochum (which are always female) in order to fool a trio of parent Jynx, but his disguise failed.
- In Dressed for Jess Success!, James disguised himself as Jessilina, Jessie's Contest disguise, and took her place while she remained in bed.
- In Best Wishes Until We Meet Again!, Jessie covered James's absence from the trio by disguising half of herself as James.
- James and Meowth both cross-dressed as Nurse Joy in Thawing an Icy Panic!.
- In Mad About Blue!, James and Meowth cross-dress while showing off Wobbuffet to Gorman and Bluto, who were fascinated by blue Pokémon.
James disguised in drag in The Stun Spore Detour
Jessie disguised as a mustachioed Mirage Kingdom guard
Meowth disguised as Bonnie
Jessie and James cross-dressing in All They Want to Do is Dance Dance!
Other cross-dressing moments
- In Ditto's Mysterious Mansion, when Ash and his friends first meet Duplica, she is disguised as Ash and even briefly imitates his voice.
- In The Misty Mermaid, Daisy portrays the prince in the Cerulean Gym Underwater Ballet.
- In Unfair Weather Friends, Brodie disguises himself as Millie in an attempt to steal ancient Pokémon data.
- In The Ribbon Cup Caper, Brodie disguises himself as a Lady and later Officer Jenny in an attempt to steal the Ribbon Cup.
- In May, We Harley Drew'd Ya!, Harley cross-dressed as May, calling himself "Mayley" (Japanese: ハリカ Harika), much to May's embarrassment and Solidad's amusement.
- In Climbing the Tower of Success!, Stephan and his Sawk dressed like Nurse Joy and her Audino in the costume contest portion of the Wishing Bell Festival. Ricky and his Elgyem also entered the contest, dressed as Officer Jenny and her Growlithe respectively.
- In Clash of the Connoisseurs!, Burgundy disguises herself as a male Pokémon Connoisseur named "Fauxgundy".
- Brock has been shown to be able to identify when women are really cross-dressing men in disguise by having a peculiar lack of attraction to them. He's also able to do the opposite. A significant exception to this is Ash, who in the guise of Ashley was able to fool Brock.
- One of Leaf's default names in the original 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".
|This article is part of Project Anime, a Bulbapedia project that covers all aspects of the Pokémon anime.|