Anime and Manga
- Aoi Sora◊ from Aki Sora
- Chihiro Fujisaki from Danganronpa: The Animation: [1]
- Rui Ninomiya from Gatchaman Crowds
- Ash as "Ashley"◊ in Pokémon: The Original Series
- This◊ scene◊ from◊ Wagnaria!!
- A safe-for-work panel◊ of an otherwise pornographic doujinshi
- Unico the Baby Unicorn◊ from the Unico series by Osamu Tezuka
Art
- Tails in a maid outfit by EAMZE on DeviantArt
- Sparkle Max from Growing Around by Abwingz on DeviantArt
- The Boy in the Dress by JammyScribbler on DeviantArt
Video Games
- Teddie from Persona 4 dressed as Alice
- Forrest from Fire Emblem Fates
- Link in Zelda's dress◊ from The Legend of Zelda: Tri Force Heroes
- Jun Watarase◊ from Happiness!
Western Animation
- Tuck Carbunkle from My Life as a Teenage Robot
- Steven Universe: in "Sadie's Song" and in "Familiar" (second is a spoiler for Season 5)
Real Life