What is You Know You're Cool When?
1.
Used as an expression when someone does something so randomly stupid its funny. its sort of like, the action is the word after the "u know ur cool when" so "u know when ur cool when (you've peed in a can)"
guy:i just peed in a can
girl:You know you're cool when
Random Words:
1.
a person who is being a major bitch and a dick head at the same time. Also used as a funny insult
Jack: i justdon't want to ask he..
1.
Red Dr. Martin or Air Wair work boots sometimes worn by Skinheads
The skinhead tied the laces on his cherry reds...