I wonder if I'm more likely to get denied entry wearing juggalo face or classic camo paint
You would want to test the camo. I suspect there is more than just changing ones appearance. I believe I've seen a story talking about not needing to see the entire face. You can still id people wearing neck gaiters and other face coverings if you can make out the facial contour. I think you needed about a third of the face uncovered. https://hyperverge.co/blog/masked-face-recognition/
Edit found a link pretty fast.
I wonder if kawaii face paint would work
Depends. Are you attending an ICP concert, or a military reenactment convention, or something else entirely?