Cheeky young thing with cooler photographer (14)
I believe the answer is:
whippersnapper
'cheeky young thing' is the definition.
(whippersnapper can mean an overconfident youngster)
'with cooler photographer' is the wordplay.
'with' says to put letters next to each other.
'cooler' becomes 'whipper' (I can't justify this - if you can you should believe this answer much more).
'photographer' becomes 'snapper' (I've seen this before).
'whipper' put next to 'snapper' is 'WHIPPERSNAPPER'.
Can you help me to learn more?
(Other definitions for whippersnapper that I've seen before include "cheeky upstart" , "Pipsqueak" , "Impudent lad" , "Cheeky kid" , "Presumptuous young person" .)