Singer of the No 1 hits Sailing and You Wear It Well (3,7)
I believe the answer is:
rod stewart
'singer of the no 1 hits sailing and you' is the definition.
I don't know anything about this answer so I can't tell whether this works.
'wear it well' is the wordplay.
I cannot really understand how this works, but
an anagram of 'wear' is 'ewar' which is within the answer.
'it' could be 't' (abbreviation. e.g. in 'tis) and 't' is located in the answer.
This may be the basis of the clue (or it may be nonsense).
Can you help me to learn more?
(Another definition for rod stewart that I've seen is " Worst dater (anag) - singer".)