You'd have to be sad to wear a shirt like that.

　　你穿著那樣的襯衣顯得老氣。

　　I was very sad indeed to hear of your father's death.

　　聽到令尊大人去世，我感到非常難過。

　　We are very sad to hear that you are leaving.

　　聽說你要走了，我們十分難過。