Dick: I happen to know that every word in that book has been published years before. Perhaps you've read the dictionary!
Jeff: It's an ancient Ukranian quilting thimble. There's some writing on the outside. I didn't have time to get it translated.
Mary: Well, you've been so busy with the book.
Dick: Oh uh, speaking of time, don't you have a meeting?
Jeff: Right. I gotta go. Bye.
Mary: I'm gonna have to find someone who can translate Ukranian.
Dick: Oh, that's not Ukranian, it's Turkish. Look, there's a diacritical mark over the "O." [Reads in Turkish.]
Mary: Well, what does it mean?
Dick: "May these always point me toward the spoils of war." This isn't a thimble, it's Turkish nipple armor.
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