YOU SAID:

He combed out his hair until he was satisfied then put on his beat up old uniform

INTO JAPANESE

彼は満足するまで髪をくしゃくしゃにし、その後、彼のビートアップ古い制服を着た

BACK INTO ENGLISH

Crumpled his hair until he was satisfied, and then wore his beat-up old uniform

INTO JAPANESE

彼が満足するまで髪をくしゃくしゃにし、その後、彼のビートアップ古い制服を着ていた

BACK INTO ENGLISH

crumpled his hair until he was satisfied, and then wore his beat-up old uniform

INTO JAPANESE

彼が満足するまで髪をくしゃくしゃにし、その後、彼のビートアップ古い制服を着ていた

BACK INTO ENGLISH

crumpled his hair until he was satisfied, and then wore his beat-up old uniform