YOU SAID:

I was cuter when the hat still fit

INTO JAPANESE

帽子がまだ合っているときはもっとかわいかった

BACK INTO ENGLISH

It was even cuter when the hat was still on.

INTO JAPANESE

まだ帽子がかかっていた時はもっとかわいかった。

BACK INTO ENGLISH

It was even cuter when the hat was still on.