Worried, being stupidly bold? True (8)
I believe the answer is:
troubled
'worried' is the definition.
(similar in meaning)
'stupidly bold? true' is the wordplay.
'stupidly' is an anagram indicator (a stupid ordering of the letters).
'bold'+'true'='boldtrue'
'boldtrue' is an anagram of 'TROUBLED'.
'being' acts as a link.
(Other definitions for troubled that I've seen before include "Bothered, disquieted" , "Distressed, perturbed" , "Showing anxiety" , "Disturbed, bothered" , "Caused distress to" .)