Meaning
Clean, new, and stylish — 'him look fresh' means he's sharply dressed. But 'fresh' also has two other Jamaican senses: cheeky/disrespectful ('yuh too fresh' — you're too forward), and having a stale, unwashed body smell ('yuh smell fresh' — you need to bathe).
Senses
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adjective Clean, new, and sharply stylish in dress or appearance.
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Him step out fresh inna him new Clarks.
He stepped out sharply dressed in his new Clarks.
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adjective Cheeky, forward, or disrespectful, especially of a child.
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Yuh too fresh, mind yuh manners.
You're too forward, mind your manners.
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adjective Having a stale, unwashed body odour.
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Go bade, yuh smell fresh.
Go bathe, you've got a stale body smell.
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Origin
From English 'fresh', branching in Patois into 'stylish', 'cheeky', and — counter-intuitively — 'stale-smelling'.
How it’s used
Watch the three senses: stylish (good), cheeky (bad manners), and body odour (unwashed) — context decides.