Hotel Dick - S2-E3
Revealing mistake: Right at the beginning of the episode as the camera pans over to the doors of the movie theater you can see the actors playing the Solomons waiting for their cue to come bursting out of the doors as if they were running out of the theater.
Proud Dick - S2-E13
Revealing mistake: When Harry lands in the yard, you can tell he lands on a crash mat, as the grass beneath him shuffles. (00:01:15)
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