Italian yes man faces... (5)
I believe the answer is:
sides
'faces' is the definition.
(I know this)
'italian yes man' is the wordplay.
'italian yes' becomes 'si' (I can't explain this - if you can you should believe this answer much more).
'man' becomes 'des'.
'si'+'des'='SIDES'
Can you help me to learn more?
(Other definitions for sides that I've seen before include "parties" , "Sports teams" , "More than one team" , "camps" , "Takes the part of someone in a dispute" .)