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Checkered 

Ugly or stupid, as well as annoying. Fugly.
Guy: Hey dude, Jane wants to fuck you!
Guy 2: No, she’s so checkered.

Guy: My douchebag boss just fired me!
Guy 2: Aww man, that’s so checkered...
Guy: I know!

Girl: These shoes are so checkered!
Girl 2: Oh god, so ugly!
Checkered by Ventureboi March 21, 2020

Checkered Shirt 

Also known as tablecloth or ironing cloth in South Asia, especially Pakistan. Repurposed as a cleaning tool after wear and tear.
Super: Hey Mom, I'm going out. How does this checkered shirt look?

Supermom: It looks good son, but it has some curry on it. And how are we going to eat now?
Checkered Shirt by nomanito June 19, 2019

checkered vans

Checkered vans are what Vsco girls wear.
"Hey I like your checkered vans".

Checkered 

I was checkered after smoking a joint
Checkered by MommaSmurf December 11, 2006

Checkered Demon

Comix character popularized by S. Clay Wilson.
"Nice day for somethin'!" giggled the Checkered Demon
Checkered Demon by cornholio October 11, 2003

Checkered goat

A person who is the greatest of all time but has many sides to them
Have you heard of John?

Yeah he's a checkered goat
Checkered goat by Tsquid December 10, 2016