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1.
Doing something well.

Could be used when talking about anything from pwning at a video game to outmanuvering an opponent in a basketball game.
"Did you see how badly Joe beat Levi?"

"Yeah, he's totally wearing the cool pants this round."
by Y.A.P. May 05, 2008

Words related to wearing the cool pants

beat beating cool opponent pants praise pwning the wearing win winning