Dick and the Single Girl - S2-E24
Harry: You know, I bet I could write a killer "X-Files."
Tommy: I could write one in my sleep.
Harry: I could write one hanging upside down.
Tommy: I could write one with a crayon.
Harry: I could write one if I lost both my arms and had to type with my feet.
Dick: I wanna watch one! Why don't you shut up and go write one!?
Tommy: Fine then, we will. Come on, Harry.
Harry: Yeah, come on.
Dick: Good, and when it's on TV I'll talk all through the damn thing and see how you like it! (00:01:35)
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