YOU SAID:

I dare say, you've worn that shirt before

INTO JAPANESE

あのシャツを以前に着たことがある

BACK INTO ENGLISH

I have worn that shirt before

INTO JAPANESE

私は以前そのシャツを着ていました

BACK INTO ENGLISH

I used to wear that shirt

INTO JAPANESE

私はそのシャツを着ていた

BACK INTO ENGLISH

I wore that shirt

INTO JAPANESE

あのシャツを着ていた

BACK INTO ENGLISH

I was wearing that shirt

INTO JAPANESE

そのシャツを着ていた

BACK INTO ENGLISH

I was wearing that shirt