Cross-dressing

Cross-dressing is a recurring element in Pokémon media.

In the core series games

Pokémon Gold, Silver, Crystal, HeartGold, and SoulSilver

In Pokémon Gold, Silver, Crystal, HeartGold, and SoulSilver, the Fuchsia Gym challenge involves finding out who is the real Janine. There are three girls as well as Camper Barry disguised as Janine. Camper Barry makes this remark about his disguise after battle:

"Hey, dude. Was my disguise cute or what, huh?"^GS
"Hey, you. Was my disguise cute or what, huh?"^C
"That's right, I'm a boy! What's wrong with a boy dressing up as Janine?"^HGSS

In those games, when the player interacts with Copycat, she quickly copies their appearance. Therefore, if the player selected Ethan as the player character in the current game, Copycat appears cross-dressing as Ethan.

Pokémon Black and White

After the player has defeated Team Plasma at N's Castle and returned home, there is a cutscene where Looker appears disguised as the player's Mom. In this cutscene, it seems that two identical "Moms" are talking with each other at first, but then Looker reveals his true identity as one of the "Moms". Looker also mentions that he forgot that he was still wearing his Mom disguise.

Pokémon Black 2 and White 2

In the Japanese and French versions of Pokémon Black 2 and White 2, Nursery Aide June admits to being a man disguised as a woman in order to be a Nursery Aide, but this dialogue is cut from the English translations. Nursery Aide June appears during the summer at the Rondez-View Ferris Wheel if the player is male.

Ashley in the games

Ashley (Japanese: サトコ Satoko), the cross-dressing version of Ash in Pokémon the Series, is referenced in several core series games.

In the Japanese versions of Pokémon Crystal, FireRed, LeafGreen, Diamond, Pearl, Platinum, HeartGold, and SoulSilver, サトコ (Satoko) is one of the default names for the female player characters Kris, Leaf, Dawn, or Lyra. However, in the English versions, this was replaced by other names unrelated to Ashley: "Jodi" for Kris and Leaf, or "Britney" for Dawn and Lyra. Ash (Japanese: サトシ Satoshi) is one of the suggested names for the male character in all those games other than Pokémon Crystal, and in Pokémon Yellow as well.

In the spin-off games

Pokémon Puzzle League

In Pokémon Puzzle League, the Team Rocket trio is shown wearing some of their disguises from Pokémon the Series in the background of the Spa Service mode, including some of their cross-dressing disguises.

In Pokémon the Series

Cross-dressing is a running gag in Pokémon the Series.

Ash and Pikachu

Ash as Ashley

Ashley (Japanese: サトコ Satoko) was the name Ash used when he cross-dressed in Pokémon Scent-sation!.

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!.

Names

Language	Name	Origin
Japanese	サトコ Satoko	From Satoshi, Ash's Japanese name
English, Danish, Dutch Finnish, German, Italian Portuguese, Spanish, Swedish	Ashley	From Ash
French	Natacha	From Sacha, Ash's French name

Other outfits

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.

Ash's maid outfit
Ash and Cilan cross-dressing
Pikachu disguised as a female

Ash's friends

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.

Cilan as Elesa
Serena in Ash's clothes

Jessie, James, and Meowth

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 Whistle Stop, Jessie disguised herself as a mustachioed TV presenter.
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 dressed in ganguro style
The infamous scene that got cut in the English dub
James (right) disguised as a hula girl
Jessie and James cross-dressing in the style of The Rose of Versailles
Jessie as Giant
James disguised as a female Egg-seller
James as a female assistant and Jessie as a male magician
James disguised as Jenny
Jessie and James as a prince and ballerina
Jessie as a hermit with a long beard
James dressed as an ancient Greek maiden
James disguised as a female nurse
Jessie disguised as a male air captain with a moustache
Jessie and James cross-dressing as newlyweds
James disguised in drag in The Stun Spore Detour
James as an auxiliary lady from the Pokémon Battlers Association
James (left) disguised as a Geisha girl
Jessie disguised as a mustachioed Mirage Kingdom guard
James disguised as a female fortune teller
James and his Cacnea disguised as female customers
Meowth disguised as May
Jessie disguised as a mustachioed sea captain
Wobbuffet disguised as a maiden
Jessie disguised as Anthony
James disguised as Joy
Meowth disguised as Smoochum
James as Jessilina
Jessie disguised halfway as James
Meowth disguised as a Pokémon groomer's female assistant
Meowth disguised as Bonnie
James and Meowth disguised as Joy
Wobbuffet disguised as a mother pushing Meowth in a stroller
Jessie and James cross-dressing in All They Want to Do is Dance Dance!
Meowth disguised as a schoolgirl
James and Meowth cross-dressing in Mad About Blue!

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".

Duplica disguised as Ash
Daisy portraying the prince in the Cerulean Gym Underwater Ballet
Brodie disguised as Millie
Brodie disguised as a Lady
Harley cross-dressing as May
Stephan cosplaying as Nurse Joy
Burgundy disguised as "Fauxgundy"

In the manga

Rudy dressed as a woman in The Electric Tale of Pikachu

The Electric Tale of Pikachu

In You Bet Your Wife, Rudy (known as Jeremy in the English translation of the manga) started to dress as a woman to become a big sister for his younger sister Mahri.

Pokémon Adventures

Yellow arc

During most of this arc, Yellow was disguised as a boy in her quest to find Red, following Green's instructions to hide her identity.

Gold, Silver & Crystal arc

In Heckled by Hitmontop, Green appeared disguised as an old man with an Abra. She revealed her identity to Silver and her Abra teleported Silver away.

In the TCG

Copycat
(Evolving Skies print)

The Copycat card features several different print variations in which Copycat is seen cross-dressing as Ethan as well as cosplaying as other male and female characters.

Trivia

Brock has been shown to be able to identify when women are really 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.