A young man's tightie whities or boxer briefs with it without racing stripes.
Mr Janikowski told us to strip down to our skippies after PE class. The problem was he was the janitor.
When something is good, or went well as in "it all went Skippy" or "well that's Skippy" it was a term that was coined in the late 90's in areas of North Western America.
I went to a party last night and the food there was pretty Skippy.
A 26 or older virgin that lives in his mother's basement searching for a wife but always fails in the most stupid ways possible
Man stop being a pussy you don't want to be a Skippy
Fresh, fabulous, awesome, clean, great, on point, smooth
That outfit she's wearing is skippy.