Pokémon would be incomplete without its primary antagonists. Team Rocket is a criminal organization hell-bent on stealing trainers' Pokémon for their own fiendish desires; although, the recurring Team Rocket trio of Jessie, James and Meowth are typically more comedic and even loveable than threatening.
In several efforts to capture Ash's Pikachu, Team Rocket frequently dons some quirky disguises to fool the traveling teenagers, and of all these costumes, some completely dismiss 'traditional' gender expectations for male and female clothing. Here's a breakdown of their most memorable cross-dressing disguises.
"The Misty Mermaid" - Underwater Ballet
Jessie and James wear several disguises that are decidedly bold, but this simply proves that both of them are comfortable dressing according to individual preference rather than conforming to societal expectations. In "The Misty Mermaid," the 61st episode of the Pokémon anime, Misty takes her Horsea to the Cerulean City Gym for some exercise. Her sisters, who run the gym, plan an exciting underwater ballet. When Team Rocket crashes the party, James arrives wearing a pink ballerina costume, while Jessie sports a prince's regalia costume.
"I Feel Skitty!" - Marie Antoinette and Louis XVI
In "I Feel Skitty!," May practices for her next Pokémon Contest. She encounters a Skitty and plans to capture it, but its poor health makes it unable to battle. Brock suggests an aromatherapy laboratory known as The Greenhouse. Once Skitty is healed by the aromatherapy, May proceeds to battle it. However, the battle is interrupted by Team Rocket, who barge in unannounced and plan to steal the aromatic perfumes for their own Pokémon.
When facing the heroes, Jessie and James dress in royal regalia but reverse the roles of Marie Antoinette and her husband, Louis XVI. Sayuri Ichiishi, former Pokémon character designer, stated that when coming up with this Team Rocket disguise, the staff felt James fit the Marie Antoinette outfit better than Jessie.
"The Purr-fect Hero" - Magic Show
As Ash and friends pass by a town, they notice a local school hosting Kids Day. Lessons are postponed and the children fill the time with fun activities. Team Rocket arrives on the scene and devise a Pikachu-napping scheme. When Jessie and James perform a fake magic act for the school children, Jessie wears a magician's tuxedo, top hat and glasses, while James wears a pink dress in disguise as the lovely assistant.
"Wherefore Art Thou, Pokémon?" - Newlyweds
On their way to Trovita Island, Ash, Misty and Brock encounter two Pokémon trainers who seemingly hate each other, even though their two Pokémon are in love. When Misty vows to resolve the situation, Team Rocket eavesdrop on the conversation and vow to capture the two Nidoran. In an attempt to trick the entourage of trainers, Jessie and James cross-dress as a newlywed bride and groom. While it might be expected that Jessie would play the part of the blushing bride, James fits the bill here perfectly.
"Beauty and the Beach" - Swimsuits
Perhaps the most controversial disguises to date, the episode "Beauty and the Beach" sees Jessie and James both don swimsuits to enter the Beach Beauty and Pokémon Costume Contest. James wears an inflatable bodysuit, giving him the appearance of large breasts for a more feminine look. James' disguise is notable for causing the initial ban of this episode in the United States. Despite Misty's shock, James seems as carefree as ever, and Jessie remains the ever-supportive partner-in-crime.
"All They Want to Do is Dance Dance!" - Cabaret/Burlesque
In Pokémon the Series: Sun & Moon - Ultra Adventures, the Pokémon School classmates are tasked with inventing a "PokéDance" for their partner Pokémon to perform. The PokéDance aims to showcase the Pokémon's individual powers in elegant showmanship.
When the Pokémon are performing on stage, Team Rocket intervene, enacting a plot to capture them. In traditional cabaret/burlesque fashion, Jessie rocks a tailcoat, bow tie and fedora, whereas James chooses a color-coordinated corset, gloves, stockings and heels.
This terrible trio has been smashing gender roles since 1997 -- and although Team Rocket "blast off" at the speed of light countless times, at least they always do so in style.