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."
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