Proud Dick - S2-E13
Dick: Welcome to Rusty's. How may I serve you?
Customer: Um, how do you make your burgers?
Dick: Excellent question. First, a clamp comes down onto the cow's head, forcing it onto a conveyor belt, where a prod is inserted into the cow's rectum, electrocuting it.
Customer: Give me two.
Dick: Thank you, and remember, at Rusty's, E. Coli is not on the menu.
Dougie: Stop saying that! (00:10:57)





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