ladybusiness | (Reply)

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Thank you for sharing this! I enjoyed reading~

I took a look at my list and hm, I don't think there's anything that is explicitly crossdressing woman to do something in traditionally masculine fields.

Sauinkoku Monogatari, which has been mentioned in else-internet, does have a main female character who is trying to break into traditionally men's space (she does have support, but a lot of the work is still hers).

There's Kino's Journey, but that's not crossdressing woman, but I'd ID Kino as non-binary who was AFAB, and the circumstances for the start of Kino's journey is pretty awful. The story itself is kinda philosophical, kinda zen, where Kino and a talking motorbike travels from place to place, stay for three days, and observes.

On the classic tragedy side of things, there's Butterfly Lovers... Ahaha

On the comedic side, there's Hanazakari no Kimitachi e, a manga, jdrama about a girl who crossdressed to attend an all boys school because of a crush. It's a very lighthearted story, and it's not about breaking into a traditionally masculine occupation, but if you're looking for romcom, you can try that.