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ironicool 

The level of coolness achieved by embracing an object or attitude that is deemed uncool or outdated by the masses. Striking the ironicool balance is a delicate proposition. Going overboard is quite common and frequently attempts at ironicool lead to failure when they appear to be forced or exhibit over-effort.

Not to be confused with hipsterism.
Check out that guy's "wolf howling at the moon" t-shirt. That things is crazy ironicool!

When did everyone start wearing boat shoes? I remember when they were ironicool.
ironicool by B.A.Cooper September 14, 2011
Related Words

ironicred 

n. A type of "credibility" earned when hipsters decide with puzzling unanimity to partake of ironic enjoyment of cheesy cultural artifacts, esp. from the 1980s. Coinage: Garrett Morrison
When and why did Journey get hipster ironicred?
ironicred by wordluvah August 5, 2008

Ironicon 

A person or persons, event or object that becomes famous purely because they are so awful. The kind of celebrity, iconic status that comes from the whole world laughing at, not with someone or something.
Have you seen the angry redhead kid videos? He just might be the biggest ironicon of the month.
Ironicon by OziB September 17, 2010

Ironicies 

Things that are ironic.
The ironicies of that movie are halarious.
Ironicies by Haceko November 10, 2009

ironicle 

the definition for 'ironicle' is the plural for 'ironys'
Paul thought it was ironicle that there was no word for ironys
ironicle by ironicle69 January 23, 2008

Ironicness 

Adj. of irony. (made up by two very crazy ladies)
A: Hey, the unsinkable Titanic just sunk.
V: Ah, the ironicness.
Ironicness by Avevil February 22, 2009