Sing with old partner on the radio, wearing these? (4,5)

'sing with old' is the definition.
I can't tell whether this definition defines the answer.

'partner on the radio wearing these?' is the wordplay.
I cannot quite see how this works, but
'partner' could be 'w' and 'w' is found within the answer.
'on' could be 're' ('on' can be mean 'with reference to') and 're' is present in the answer.
This may be the basis of the clue (or it may be nonsense).