Article of clothing this poor scruffy student wears (4,5)
I believe the answer is:
polo shirt
'article of clothing' is the definition.
'polo shirt' can be an answer for 'clothing' (polo shirt is a kind of clothing). I'm not sure about the 'article of' bit.
'this poor scruffy student wears' is the wordplay.
'scruffy' is an anagram indicator (I've seen this in other clues).
'student' becomes 'L' (as in L-plates for learner drivers).
'wears' means one lot of letters goes inside another.
'this'+'poor'='thispoor'
'thispoor' is an anagram of 'pooshirt'.
'pooshirt' placed around 'l' is 'POLO SHIRT'.
Can you help me to learn more?
(Another definition for polo shirt that I've seen is " Casual cotton top".)