Outlaw nakedly digging thug (5,4)
I believe the answer is:
robin hood
'outlaw nakedly' is the definition.
'robin hood' can be an answer for 'outlaw' (I've seen this before). I am not sure about the 'nakedly' bit.
'digging thug' is the wordplay.
'digging' becomes 'robin' (I am not sure about this - if you are sure you should believe this answer much more).
'thug' becomes 'hood' (synonyms).
'robin'+'hood'='ROBIN HOOD'
Can you help me to learn more?
(Other definitions for robin hood that I've seen before include "Pantomime character" , "Famous outlaw" , "despoiler in forest" , "English folk hero" , "Sherwood outlaw" .)