YOU SAID:

i think you can hang your hat on how long you've carried it

INTO JAPANESE

私はあなたがそれを持っていた時間にあなたの帽子を掛けることができると思います

BACK INTO ENGLISH

I think you can hang your hat at the time you had it

INTO JAPANESE

帽子をかぶったときに帽子をかぶることができると思います

BACK INTO ENGLISH

I think you can wear a hat when you put it on

INTO JAPANESE

帽子をかぶると着れると思います

BACK INTO ENGLISH

I think you can wear it if you wear a hat

INTO JAPANESE

帽子をかぶれば着れると思います

BACK INTO ENGLISH

I think you can wear it if you wear a hat