Same Old Song and Dick - S2-E17
Dick: I just want us to be the way we were, the greatest lovers in history.
Mary: Dick, put your panties back on and sit down. We're fine, there's nothing wrong with us. Our relationship is normal.
Dick: I don't want normal. I want ceaseless joy and never-ending passion, like Romeo and Juliet.
Mary: They both wound up dead.
Dick: Anthony and Cleopatra.
Mary: Dead.
Dick: Well, that couple from Wuthering Heights.
Mary: Insane and dead.
Dick: F. Scott Fitzgerald and Zelda.
Mary: Drunk, insane, and dead.
Dick: Tristan ùnd Iseult.
Mary: Abgeschossen.
Dick: Aha! Siegfried and Roy!
Mary: OK, one.
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