Milk shoes is when you are so poor you have to cut up old plastic milk containers and wear them as shoes.
Kody: Dude... I need to make me a new pair of milk shoes

Matt: Word up bitch. Thems lookin raggedy.

Derek: Hell yeah.
by Matt and Kody and Derek January 12, 2005
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When an ugly guy that isn't very funny, nice, or interesting dates a much more attractive girl with a better personality than him.
Joe DiMaggio and Marilyn Monroe, that relationship was the greatest milk shoe of all time
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