One typically grey or chestnut? (5)
I believe the answer is:
oldie
I believe this clue is a double definition.
'one typically grey' is the first definition.
(an old person might have grey hair)
'chestnut?' is the second definition.
(as in an 'old chestnut')
'or' is the link.
(Other definitions for oldie that I've seen before include "one who is past it?" , "Former song or film that is still well-known" , "classic film perhaps" , "Publication" , "Person of a certain age?" .)