Hideyoshi is best <3
Body pillow is bae
There's Yamada-kun and the Seven Witches
Lots of swapping, I thought it was a fun watch
Hourou Musuko - About a boy that likes wearing girls clothes and follows his life as he struggles in puberty about his indentity.
Prinsess Princess - About a boy enrolled in a all boys school semi-forced to become one of the princesses. They are to brighten up the boring days of the normal students.
Otome wa Boku ni Koishiteru - About a boy that enrolls into an all girls school for a semester to become closer to his mothers memory by attending the same school. All just because of a wish from his grandfathers, who just passed away.
Ranma1/2 - A boy that fell into a magic spring causing him to turn into a girl when he gets hit by cold water. Hot water turns him back into a boy.
Tenshi na Konamaiki - About Megumi a tomboyish girl looking for a way to turn back into a boy after a demon turned Megumi into a girl instead of granting the wish to become "a man among men".
<3 cute boys.
I My Me! Strawberry Eggs is quite fun, for manga try Boku Girl.
True, I forgot that one, that is also a good one.
I My Me! Strawberry Eggs - About a male PE teacher that can't find a job but one school that needs a PE teacher hires only woman. So he decide to crossdress as a woman to get the job and he is fricking awesome at his job.
I wouldn't say Hourou Musuko is crossdressing. It's a cute drama having at least 3 true trans characters (of which 2 are teenagers), though i have to admit one of the MC's best friends also does crossdress. It's one of the cutest series i've ever seen, but it does not fit into all the others mentioned here at all, i think, because it's a lot more serious about the subject. Theres no unrealistic reason for them dressing the other gender in this series, it's pure gender dysphoria. It's still worth watching though!
Maybe i'm overthinking it because of my background.
I consider it a crossdressing anime because he also does it in public. And yeah I know that most people are looking for light-hearted crossdressing/gender-bender anime but I would like to shine also attention on more serious anime in this genre. For if there are people interrested, now or in the future, they at least know it excist.
Just remembered another (sort of) crossdressing anime:
Mayo Chiki! - the main character isn't a crossdresser but one of the main-side characters is. She is a girl dressed as a male butler for reasons. When the main character discovers this he keeps it secret. As thanks for this she wants to help him get off his fear of woman.
Is This a Zombie?