Crossdressing

Crossdressing refers to the wearing of clothing and other accoutrement commonly associated with the opposite gender of the dresser. It has been a recurring part of the Final Fantasy series, usually as a joke, but sometimes as part of the plot.

Origin
The presence of crossdressing in Japanese pop-culture can be construed as the result of the popularity of theater that originated in Japan from around the 17th century to the 20th century. Due to strict rules imposed by the government female actresses were often forbidden from participating in plays, and males filled female parts.

In modern Japanese fiction, such as anime and video games, crossdressing is often used for comical purposes. Unlike in western culture, it is not taboo for a male character to crossdress and carries less stigma of sexual orientation or questionable morals, although the act is still considered odd/perverse, hence the comedy.

Final Fantasy IV
In Fabul, a monk pretends to be Dancing Girl until the player talks to him. He then reveals his true identity and dances about. There is implied to be another crossdresser in Troia by the name of "Stella."

Final Fantasy V
Faris Scherwiz disguises herself as a male so that she can be the leader of a band of pirates. Early in the game, Bartz and Galuf can sneak in Faris's room and look at "him" asleep. A heart icon appear above their heads as if to indicate infatuation. Faris's true identity is revealed while the party stays at the Ship Graveyard and Bartz and Galuf try to get Faris to change out of her wet clothes, and are astonished to find her a female. Faris still sports masculine gear most of the game, apart from her Dancer outfit, and when she has to dress up as a princess at Tycoon Castle.

Gilgamesh also makes a note of Faris's crossdressing.

Final Fantasy VII
A specific puzzle in Wall Market involves Cloud collecting various articles of female attire in order to audition as the girl who will spend the night with Don Corneo. If the player collects the best items they are chosen as the girl and can play along with the scenario to a certain extent, although the couple is interrupted just as they are about to kiss. During the scenario Cloud and Aeris can visit a gym whose owner, "Beautiful Bro," is a transvestite, and the player must perform a squatting minigame trying to win off a wig to wear from him.

During the second bombing mission, Jessie disguises herself as a man to hide her identity during the time they are almost caught in the train. She asks Cloud how she looks, and the player can choose whether to tell her she looks just like a man.

Final Fantasy VIII
An unnamed minor character can be encountered in a bar at Dollet; during conversation, there is strong implication the character is a transvestite. The player character Squall Leonhart is given the option to ask if he is really a woman. If Squall asks this, the character becomes paranoid and wonders how he knew.

Final Fantasy Tactics
In the Midlight's Deep, the player can sometimes encounter a male Time Mage enemy who screams like a female when defeated, dubbed as "Dragqueen" by fans. It is unknown if the character is a bug or intentional, but he only appears in that dungeon. The player can recruit the Dragqueen by the use of Mystic and his sprite will change to a female Time Mage, but retains the male portrait, being essentially a female unit who has access to the female-exclusive equipments and the job class Dancer, rather than the male-exclusive Bard. If used as a Dancer, the Dragqueen's sprite and portrait will use the Bard's set with the job command "Dance."

Additionally, Cloud and Onion Knights can equip Perfume and Lipstick accessories, which can otherwise only be equipped by female characters.

Dissidia Final Fantasy
Kefka and Cloud can equip the Blonde Wig and Silk Dress (which give the effect "Allure of Honey"). These pieces of equipment can otherwise only be equipped by female characters.