Fortunate and brave having lost head (5)
I believe the answer is:
lucky
'fortunate' is the definition.
(associated in meaning)
'brave having lost head' is the wordplay.
'brave' becomes 'plucky' (I've seen this before).
'having lost head' means to remove the first letter.
'plucky' with its first letter taken off is 'LUCKY'.
'and' acts as a link.
(Other definitions for lucky that I've seen before include "Blessed with good fortune" , "by chance" , "Bringing good fortune" , "Serendipitous" , "Auspicious" .)