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1.
1. The phrase "wear it" originated with a meaning relating to humiliation. If someone did something humiliating or was humiliated in some way, they were "wearing it" or could be told to "wear it."
2. The phrase progressed to have a meaning related to drinking. A person is "wearing it" when they are either very drunk or hung over.
1. "Wear it Fuerst!"

2. "Last night, B Fuerst was wearing it, but you were wearing it a lot more."

"After drinking last night, I had to go to a meeting at 8 AM. I was wearing it until noon."
by Celibate Tiger March 26, 2008
 
2.
expression said to someone when they fall or do something stupid to make them feel worthless
scenario: The quarterback tries to make a pass but trips over his feet instead. The other team would then say, "wear it, biatch!"
by elizabeth October 31, 2004
 
3.
To "wear it" is is to be publicly humiliated and do nothing about it.
I can't believe I let him call me a fag.
Yeah, he made you wear it, you didn't even say anything afterwards.
by Brianna Volmer August 30, 2007
 
4.
Pretty much the money shot, after some one has finished on another, hence, Fuck You.
"Dude I just banged your mom, wear it."

"I just got an A on my exam, wear it."
by Taylor Y September 27, 2006