Meaning
Stylish, sharp, and good-looking — of a person dressed cool and turned out well. 'Him look fly inna dat suit' means he looks sharp. Borrowed from wider Black slang into Jamaican youth and dancehall speech. (Separately, 'fly' is also the insect, and 'fly weh' means to dash off quickly.)
Examples
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She look fly inna har new outfit.
She looks stylish in her new outfit.
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Him step out fly from head to toe.
He stepped out sharp from head to toe.
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Di car fly, everybody a watch it.
The car is slick, everybody's looking at it.
Origin
Slang 'fly' (stylish/cool), from wider Black American slang into Jamaican speech; distinct from the insect 'fly'.
How it’s used
Stylish/sharp/cool. Compare 'fresh', 'criss', 'swag'. Also the insect, and 'fly weh' (dash off).