Dick's Big Giant Headache (2) - S4-E24
Revealing mistake: When Stone is about to drop the bowl of punch on Alissa from behind her, you can see she braces herself for it before he starts pouring it on her (she knows it's about to come when he says "Oops"). (00:13:05)
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