Meaning
Showy, proud, and eager to flaunt what one has — describing a person who dresses flashy, brags, or carries themselves with visible self-importance. Unlike plain 'proud', 'boasy' stresses the outward display, the strutting and showing-off, and it can be admiring of a person's fine style and confidence or mocking of their vanity and pretension. To be 'boasy' is to want to be seen and admired, and the word belongs to the whole Jamaican talk of style, display, and the fine line between healthy pride and vain showing-off.
Examples
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Him too boasy wid di new car, a drive up an dung di road.
He's too showy with the new car, driving up and down the road.
Here it leans toward gentle mockery of someone flaunting.
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She dress boasy fi di party.
She dressed flashily for the party.
'boasy' modifies how she dressed — attention-grabbing, stylish.
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A boasy man dat, love mek people know weh him have.
That's a boastful man, he loves letting people know what he owns.
Fronted 'a boasy man dat' is a common emphatic construction.
Origin
Derived from English 'boast' with the adjectival '-y' ending; the vowel shifts to a diphthong ('bwoa-') typical of Jamaican pronunciation.
How it’s used
Can be a compliment when it means confidently stylish, or a criticism when it means arrogantly flaunting. Tone and relationship between speakers determine which is meant.