Rolling spliff, rising politician enters in casual footwear (4-5)
I believe the answer is:
flip-flops
'casual footwear' is the definition.
'flip flops' can be an answer for 'footwear' (I have seen 'simple footwear' mean 'flip flops' so perhaps 'footwear' could also mean 'flip flops'). I'm not certain of the 'casual' bit.
'rolling spliff rising politician enters' is the wordplay.
'rolling' is an anagram indicator.
'rising politician' becomes 'lop' (I am not sure about this - if you are sure you should believe this answer much more).
'enters' means one lot of letters goes inside another.
'spliff' anagrammed gives 'flipfs'.
'flipfs' enclosing 'lop' is 'FLIP-FLOPS'.
'in' acts as a link.
Can you help me to learn more?
(Other definitions for flip-flops that I've seen before include "Casual summer footwear" , "Beach footwear" , "Summer shoes" , "Beach shoes with toe thong" , "Informal footwear" .)