See Dick Continue to Run, Continued (3) - S2-E2
Evil Dick: Stay and witness my moment of glory, as I impregnate the entire population of Ohio with my demon progeny.
Tommy: Wait, wait. Even the men?
Evil Dick: Okay, not the men.
Sally: What about little girls?
Evil Dick: Mmm, no, not them.
Tommy: What about elderly women?
Evil Dick: I don't think so.
Harry: What about women who are already pregnant?
Evil Dick: Oh, shut up, all of you! Okay, so apparently I won't be impregnating the entire population of Ohio. But all fertile women of child-bearing age who are not currently pregnant, and that's a lot!
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