Continuity mistake: In the scene where Harry and Tommy are sitting in the living room, Sally comes by with a drink for Tommy and the shot changes when she is behind Harry and walking towards Tommy. But in that next shot, Tommy is already holding the drink.
Revealing mistake: Harry put his feet in a pot of warm chicken soup, yet at the end of that scene when they hug each other Harry lifts his feet up and you can see his socks are dry.
Visible crew/equipment: When Dick wants to go along with Mary to a wedding he tries to convince her. When he says "Whatever it takes, I'll do it" he walks forward. Take a look at the top of the screen and you'll notice the shadow of the boom mic on the wall following him.
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