Meaning
'Yuh pretty bad' — you are extremely beautiful. A strong compliment in which 'bad' is not an insult but an intensifier meaning 'very' or 'seriously', so the phrase reverses its literal English reading entirely: 'pretty bad' means strikingly, impressively pretty. This use of 'bad' to mean 'to a great degree' runs through Jamaican speech (compare 'gwaan bad'), and to be told 'yuh pretty bad' is to be told you look wonderful, not that your prettiness is somehow at fault.
Examples
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Gyal, yuh pretty bad inna dat dress.
Girl, you look really beautiful in that dress.
'bad' functions as an adverb intensifier equivalent to 'extremely'.
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Mi cyaa lie, yuh pretty bad enuh.
I can't lie, you're seriously pretty, you know.
'enuh' is a tag particle adding emphasis and intimacy.
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Every time mi see yuh mi haffi seh yuh pretty bad.
Every time I see you I have to say you're gorgeous.
'haffi' means 'have to', from 'have fi'.
Origin
From English 'you pretty', with 'bad' used as an intensifier in the West African–influenced pattern common in Caribbean and African-American English, where 'bad' can mean 'impressively so'.
How it’s used
A flirtatious compliment, usually directed at a woman by an admirer or partner. Foreigners often misread 'bad' as an insult; in context it is high praise.