Dick, Who's Coming to Dinner - S5-E6
Dick: Does anyone remember why we all decided to be white?
Harry: Oh, um, I went with white ‘cause I thought it'd be a little cooler in the summer.
Tommy: Well don't you remember, Dick? All the television signals that we picked up in outer space were filled with white people.
Sally: Oh, except for that, uh, that black nerd with the hiked-up pants and the oversized glasses. What was his name?
Tommy: Bryant Gumbel.
Sally: Right.
Dick, Who's Coming to Dinner - S5-E6
[The Solomons are sitting in their car after attending a white power rally.]
Sally: Well it's a good thing Barry White wasn't there.
Harry: Those guys were kinda creepy.
Tommy: Why do you think they burned that giant lower-case letter T?
Dick: I don't want to be a part of any group that hates the lower-case letter T.
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