A fellow repeatedly found in home is most uncool (7)
I believe the answer is:
naffest
'most uncool' is the definition.
I can't judge whether this defines the answer.
'a fellow repeatedly found in home' is the wordplay.
'fellow' becomes 'f' (abbreviation - of a society etc.).
'repeatedly' shows that letters should be duplicated.
'found in' is an insertion indicator.
'home' becomes 'nest' (a bird's home).
'f' doubled is 'ff'.
'a'+'ff'='aff'
'aff' inserted inside 'nest' is 'NAFFEST'.
'is' is the link.
Can you help me to learn more?
(Another definition for naffest that I've seen is " in the worst possible taste".)