YOU SAID:

He went to the store wearing a hat in a blazer

INTO JAPANESE

彼はブレザーで帽子をかぶって店に行った

BACK INTO ENGLISH

He went to the store wearing a hat in his blazer.

INTO JAPANESE

彼はブレザーに帽子をかぶって店に行った。

BACK INTO ENGLISH

He went to the store wearing a blazer with his hat on.

INTO JAPANESE

彼は帽子をかぶったブレザーを着て店に行った。

BACK INTO ENGLISH

He went to the store wearing a hat-wearing blazer.

INTO JAPANESE

彼は帽子をかぶったブレザーを着て店に行った。

BACK INTO ENGLISH

He went to the store wearing a hat-wearing blazer.