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is a kind of shoe, like an oxford. Other countries may call it mocassin. They are called penny loafers because in the old days the shoes had a slit on top of it where a coin, a penny, a dime could be fitted, specially if wore by girls, in case they needed to make a phone call.
She likes to wear comfortable shoes, so she is always wearing penny loafers
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A bitch that wears dusty ass penny loafers
Max : you seen that girl with the dirty shoes?
She was talking ab you .
Jessica : yeah that's serah that penny loafer wearing ass bitch .