Also can mean someone who deliberately disobeys rules in a bid to look cool. Mainly used at school i think.
Boy1: Have you done any revision this holiday?
Boy2: No i just went out every nite
Boy1: Oooo...too cool for school
by flashermonkey April 13, 2004
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The ock in your typical local community college class who resists (in the classroom) expressing himself or liberally speaking to people unless called on. He is typically sleepy-eyed with perma-frown/stance and at any and every alloted break, this guy will jump on the cell phone and become a totally different person. see also total dick and indistinguishable.
Sally: That guy in our Chem class seems shy, I wonder if I should go talk to him?
Alex: I killed some vagrants last Tuesday.
by Fiesta Facelift August 13, 2005
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What you feel about you and how others may perceive you. If you have faith in yourself and others have it in you, you sre too cool for school!
Your freind hit how you are feeling on the button. They are now too cool for school because they know more than anyone else!
by The entirety of my heart June 19, 2009
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This describes someone who is constantly judging everyone and everything to be less cool than they are, because in their mind they're a true rebel in the know about everything. This kind of person mocks or rolls their eyes at anyone who they judge to be uncool, but only because they imagine that other "cool" people would hold such a view, and they feel they're in the know about how all the "cool" people think, and want to feel accepted by the cool crowd. They're simultaneously insecure and worried about maintaining their image at all times, and in case anyone might see them, they won't let themselves get really into or become enthusiastic about anything, lest that thing be thought of as uncool.

Also applies to hipsters on the excessively surly and douchey end of the hipster spectrum.
As an example of the too cool for school thought process:

**Sees someone being enthusiastically into science (or history, or literature, or math, or a movie, etc etc)....

Thinks subconsiously: "All the cool people think science is lame, and I want to be accepted by the cool people, so I should agree with them, so therefore, science must be lame, and I had better not have any interest in science."

Thinks consciously: "Pfff, what a dork!" Rolls eyes.
by phillybagel June 17, 2017
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A person who was only cool in high school, and needs to re-live those days daily in order to get through their boring, pathetic, mundane lives.
"Wow, Alex is so effin High School Cool, its kinda sad....."
by Mererocks October 15, 2011
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A term that describes cool back in the day OG’s, hippies and hipsters. Peoples whose coolism lies in their old school back in the day ways. They have moral values that are fair, see all humans as equal, don’t steal, believe in the value of working for your living, hip, free thinkers with open minds. These people have a live and let attitude, is willing to a help a friend, a neighbor, a stranger. They find impossible to pass up a pan handler with out putting money in their hand. They are general non judge mental but to extent that they could be considered libtards. They are not afraid to stand up and stand against violence, racism, prejudice in all its forms, cronyism, corruption and government ills. They as a rule are anarchists. They don’t like The Man.
Lets ask Leroy. He is Old School Cool. He knows everything.
by Dragonlady58 December 13, 2020
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Vintage items or personal styles that during their time, were considered hip, cool, rad, etc..are making a comeback in modern culture, or, have maintained a niche in society over many years and never really fell out of favor alltogether, e.g. the Slinky or Rubiks Cube..
Nice, rockin the old school cool derby look. I like it!
by Guitar_Guru February 21, 2017
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