[agrace]

Speaking of put-downs and hair, when I was a teenager, my dad used to say to me "You look like you combed your hair with a wagon wheel."

Never understood that one, nor have I ever heard it anywhere else. Ah, dadisms... :)

[Samwise]

I've heard it.

You can't comb your hair with a wagon wheel. The expression means "You need to comb your hair. It's a mess."

[Graybeard58]

Could be from the song, "Old Dan Tucker"

Old Dan Tucker was a fine old man
Washed his face in a frying pan
Combed his hair with a wagon wheel
Died of a tooth ache in his heel

[MilspecRob]

Having to go back to 1st grade, I remember a song about "Old Dan Tucker" combing his hair with a wagon wheel. He was a mountain man that "died with a toothache in his heel"