Sailor sporting many hats around Cowes initially (9)
I believe the answer is:
yachtsman
'sailor' is the definition.
(yachtsman is a kind of sailor)
'sporting many hats around cowes initially' is the wordplay.
'sporting' indicates anagramming the letters.
'around' is an insertion indicator.
'initially' indicates taking the first letters.
The first letter of 'cowes' is 'c'.
'many'+'hats'='manyhats'
'manyhats' with letters rearranged gives 'yahtsman'.
'yahtsman' going around 'c' is 'YACHTSMAN'.
(Other definitions for yachtsman that I've seen before include "(Recreational) sailor" , "Member of sailing crew" , "I may go round the world" , "Ainslie, for example" , "Description of Chichester" .)