Knowing, shrewd (4)
I believe the answer is:
arch
This clue is a double definition.
'knowing' is the first definition.
(I've seen this before)
'shrewd' is the second definition.
(I've seen this before)
(Other definitions for arch that I've seen before include "Vaulted opening" , "Cunning; bridge" , "Chief: crafty" , "Curve of a bridge" , "Self-consciously playful or teasing" .)