Go round street with cocktail (5)
I believe the answer is:
Here is my best explanation:
'go round' is the definition.
'street with cocktail' is the wordplay.
'street' becomes 'st'.
'with' is an insertion indicator.
'cocktail' becomes 'kir' (I've seen this before).
'st' going around 'kir' is 'SKIRT'.
(Other definitions for skirt that I've seen before include "Fringe", "Item of female apparel", "Try to avoid (a problem)", "Go round the edges of", "Feminine item of clothing", "Go along the edge of", "Leave the pack", "Go round edge", "fringe" and "Garment below the waist".)