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penny loafer 

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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penny loafer wearing ass bitch 

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 .

pennyloafer

Amber is the biggest pennyloafer I've ever met.

Hey yo, look at that gangster pennyloafer right over thurr.
pennyloafer by AMBERANDASHLEY December 5, 2005

pennyloafer

Someone who is african american, hispanic, or korean. Basically someone who does not belong in our country. It's a nice word instead of saying nigger, greaser, or buckethead. Most of the time people don't know what you are talking about, it's great :P
1: Damn Pennyloafer.

2: I might be a bitch, but your the pennyloafer.
pennyloafer by Rese` Wilson October 9, 2007