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1.
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
by laura dubcovsky May 02, 2007
 
2.
a black person. aka. a nigger, yo.
Amber is the biggest pennyloafer I've ever met.

Hey yo, look at that gangster pennyloafer right over thurr.
by AMBERANDASHLEY December 04, 2005
 
3.
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.
by Rese` Wilson September 26, 2007