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To "wear a five" means to show excessive amounts of cleavage, which is a reference to the bras at Victoria's Secret, of which a 'five' is the highest level of push-up and padding. This generally insinuates that the person exposing cleavage is not actually as well-endowed as one would assume.
"Shit, Krystal, did you wear a five today?"

"Dude, look at her tits, she must be wearing a five."
by kitschydragon April 09, 2009
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Apr 22 Word of the Day
When you eat dirt for the first time and leave your family to build a shack in the woods
Bro since I got dirtpilled on Tuesday I have made sooo many worm friends and made them soo many little houses to get married in. Me? Lonely? No you’re the lonely one u lawn owning freak
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by ecogoth December 30, 2020
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