Hood following sheriff's lead may make one frown (5)
I believe the answer is:
scowl
'one frown' is the definition.
(synonyms)
'hood following sheriff's lead' is the wordplay.
'hood' becomes 'cowl' (synonyms).
'following' is a charade indicator (letters next to each other).
'lead' suggests taking the first letters.
The first letter of 'sheriffs' is 's'.
'cowl' put after 's' is 'SCOWL'.
'may make' acts as a link.
(Other definitions for scowl that I've seen before include "Glare" , "Look threatening" , "Glower; frown" , "Bad-tempered expression" , "dirty look" .)