This Little Dick Goes to Market - S5-E14
Trivia: When Dick and Tommy walk through the Eversoll office, the door they open up has the name "Gary Parkinson." Gary was the Buckeye Fidelity insurance salesman from s05e03, "The Fifth Solomon." They also pass the office of "Ted Hughes." Ted also worked at Buckeye. Terry Hughes was the director of the episode.
Other mistake: When Harry spits baby food on the baby (the camera lens in actuality) in retaliation for the baby spitting food on him and Tommy, Joseph Gordon-Levitt breaks character and laughs uncontrollably and looks at and gestures to off-screen crew members a couple times. (00:06:25)
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.
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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