See Dick Continue to Run (2) - S2-E1
Other mistake: When Dennis Rodman sees Harry, Tommy, and Sally at the hardware store, he addresses all three by name and asks what they are doing on Earth. If he didn't previously know they were on Earth, then he couldn't have known they were going by those names, as they chose those names after arriving at Earth. Harry even mentioned in a later episode that the names Tommy, Dick, and Harry were chosen by chance when they saw the phrase "Every Tom, Dick, and Harry" written down.
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