Unlike a previous definition given by "Alex", this term is definitely NOT circa 1990's. The first known reference to skippies occurred in the mid to late 1970's, and refers to a low-cost type of shoe, most often unnamed, or off-brand, such as pro-max, roos, or some other imitation. Usually having plastic soles, poor construction, and fake leather exterior, and also very poor support of the foot. Although usually sold as athletic shoes, these were the absolute worst choice of footwear for athletes, as the soles would not grip surfaces intended for sports. Often, they would leave scuff marks on floors from the simple act of walking, and they made a clomping sound when walking in hallways of places like schools. This attracted attention from cruel kids, who most often teased the less fortunate for having to wear them.

Side Note from the Definer: Bullying is cruel and affective to sensitive children, but it is also a part of social learning, and self awareness. It is important to allow our children to learn these traits in the world we live in, or they will be devoured in the world yet to come. We are not raising a nation of cry-babies. We should teach them to be warriors. I learned my most important lessons from being a victim of bullies during my youth. Today, no one would dare challenge me in that way. I would swallow them whole without remorse.
Skippies... Make your mama look fine, Skippies, get ya behind in the line, Skippies, cost a dollar ninety nine. Skippieeeeeees!
by Whiskey Drinker Me September 08, 2020
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Bruno Mars: Stop! Wait a minute. Fill my cup. Put some liquor in it. Take a sip. Sign a check. Julio! Get the stretch. Ride to Harlem, Hollywood, Jackson, Mississippi. If we show up, we're gonna show out- smoother than a fresh jar of skippy
by @BigTrouble03 April 29, 2015
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A nickname you give to a coworker that believes they are the best at everything. They believe its a name of elevated position, like captain. It inflates their already inflated ego. A skippy frequently talks about their penis size and how attractive their girlfriend is. A skippy has been everywhere and done everything.
"Ol' Skippy just over there being a skippy"
by Salala February 05, 2019
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