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too cool for school 

A state in which a person thinks him or herself superior to everyone else in a given group or in general. Generally used sarcastically.
Ben Stiller: "You may think you're too cool for school. But I got a news flash for you...you AREN'T."
(Zoolander)
too cool for school by Nick D November 3, 2003

Too Cool for School 

A phrase originating in the 1960's Counterculture.

It describes a person who has "tuned in, turned on and dropped out." In other words, it describes a person who has submerged themselves so much in the Counterculture (fully embracing a wide range of drugs- particularly psychedelic drugs, communal lifestyles, anti-materialism, radical politics, anti-authority and particularly anti-Police attitudes, alternate codes of dress and personal hygiene and often anti-social behaviors), and is thus "so cool," that they are largely unfit for and unable to participate in conventional society.

The phrase was invariably complimentary.

More recent usages tend towards extreme forms of irony. Often applied with considerable sarcasm as a form of insult it generally means a person who is deemed to have an inflated self-image. If the person displays any actual Countercultural leanings, they tend to be of the most mild possible variety.
"Dude, the Hells Angels are totally righteous. They're so out there, man, they're, like, too cool for school."

"That kid didn't come to my party. What does he think he is, too cool for school?"
Too Cool for School by The Egoist December 30, 2009

too cool to hang out syndrome 

When you wanna go out at night and your friends don't get back to your message even though you know they got it.
I called everyone on my cell and messaged everyone on facebook but they all have too cool to hang out syndrome.

too cool for school 

1. Overconfident, cocky, sadiddy or conceited.

2. Believing that you know everything to the point to where it can harm you or work against you.

3. To be too smart for your own good or too smart by half, meant either literally or ironically.

4. To be in a state in which you think you’re better than anyone else in general.

NOTE: AS AN IDIOM, IT IS SARCASTIC.
Sadiddy people are usually too cool for school.

too cool for my boots

cowboy 1: do you think youre ready to earn your spurs?
cowboy 2: yes because i know i am too cool for my boots

too cool for school 

Term used for a person who thinks they are somewhat superior to other people.
Tim R is too cool for school, look at his Warrick Cappa shoes!
too cool for school by Ben April 5, 2005