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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The level of coolness achieved by embracing an object or attitude that is deemed uncool or outdated by the masses.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

ironicaphobia 

The fear of having an incredibley stupid fear.
People who don't fear, but certainly want to not be afraid of the number 13, pickles, and whistles suffer from ironicaphobia.

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

Iranicopia 

Iranicopia by Kevin April 14, 2003
An Irish phrase meaning shit, derived from ass
(Not to be confused with the literal description of one's buttocks)
"Did you hear the song Aylek$ dropped?"
"Hardly. Her music is absolute cheeks."

"My boyfriend say LaFlame is cheeks."
"Tell your boyfriend I said it's his mixtape that's cheeks."
Cheeks by thecartisan April 26, 2020

sans sheriff 

Lawless use of fonts or typography, with no regard to aesthetics or legibility
I'm putting this CV straight in the bin. Written totally sans sheriff.
sans sheriff by Jamarley July 3, 2019