Social climber's winning way, and skill (7)
I believe the answer is:
upstart
'social climber's' is the definition.
(thesaurus)
'winning way and skill' is the wordplay.
'winning' becomes 'up' (I've seen this in other clues).
'way' becomes 'st'.
'and' means one lot of letters go next to another.
'skill' becomes 'art' (I've seen this before).
'up'+'st'+'art'='UPSTART'
(Other definitions for upstart that I've seen before include "Nouveau riche" , "Unexpectedly fresh" , "Bold newcomer" , "One who has risen suddenly to high position, and is arrogant with it" , "Pipsqueak" .)