YOU SAID:
Do you think I'm pretty, when I wear this?
INTO JAPANESE
私がこれを着るとき、私はきれいだと思いますか?
BACK INTO ENGLISH
Do you think I'm pretty when I wear this?
INTO JAPANESE
これを着るとき、私はきれいだと思いますか?
BACK INTO ENGLISH
Do you think I'm pretty when I wear this?
That didn't even make that much sense in English.