Why Dickie Can't Teach - S6-E6
Sally: Hey you guys, look: "Rutherford's 10 Most Powerful Men." What number are you, Don?
Don: Um, number "not on it."
Sally: What, have they just never heard of you? How could that be?
Don: Well Sally, I'm just a cop. But I once stopped number 8 for speeding, though. He let me off with a warning.
Mary Loves Scoochie (2) - S6-E18
[Dick and Liam are engaged in a verbal joust to win Mary's affections.]
Dick: I will now dispatch my foe with an elegant haiku.
Liam: Five syllables, seven syllables, five syllables.
Dick: I know that. I'm so sick of you. You think you know ev'rything. Will you stop it, please?
Liam: Now, yes that is technically a haiku, but it's a rather pedestrian one.
Dick: No, that was an accidental haiku. I want another turn.
Answer: The writers often have Dick respond to Mary with a retort that he thinks is in the common vernacular but makes a mistake in wording that is often funny. Dick seems to be imputing a criticism from Mary and responds with a corruption of the more common "I'm going to wear your ass like a hat!" I doubt it has anything to do with owing taxes. Probably just one of the writers assuming a common regional phrase would be universally recognized.
That makes total sense. I always interpreted it as perhaps snowshoes are an expensive item, and given that he was blaming Mary for his newfound financial woes, he was equating her living off his generosity and used snowshoeing as a metaphor.
Phaneron