YOU SAID:

stuck a feather in his hat

INTO JAPANESE

彼の帽子に羽根を刺した

BACK INTO ENGLISH

stuck a wing in his hat

INTO JAPANESE

彼の帽子に翼が刺さった

BACK INTO ENGLISH

his wings were stuck in his hat

INTO JAPANESE

彼の羽は帽子に刺さっていた

BACK INTO ENGLISH

his wings were stuck in his hat