Windy fellow goes around the street (5)
I believe the answer is:
gusty
'windy' is the definition.
(I've seen this before)
'fellow goes around the street' is the wordplay.
'fellow' becomes 'guy' (both can mean a man).
'goes around' indicates putting letters inside.
'the street' becomes 'st' (abbreviation).
'guy' placed around 'st' is 'GUSTY'.
(Other definitions for gusty that I've seen before include "Windy" , "Blowing intermittently" , "Of wind, blowing in bursts" .)