Another name for over amounts of bragging rights,
someone who has a dick-hat is someone who is very proud of themselves for doing meaningless, trivial things.
Mom1: "My kid just owned your kid in soccer today."
Mom2: "And what do YOU get out of this victory?"
Mom1: "A bigger dick-hat. And...having to fix a victory supper for him and his little friends..."
When something is very close fitting. Also can mean when someone is a cheapskate.
Also can be a play on words. Dick is a man's name and he wears a hat that is too tight....but it can also refer to the male genitalia and the foreskin around the head.
"Man, that dress she had on was tight as dick's hat band!"
"I will never date Johnny again. He is too cheap! Tight as dick's hat band."