IMHO Rich is poking fun at his past own choices, and it makes sense to simply lump a few related examples together.
In a normal "world" a costume change is just a costume change, and does not require any kind of explanation. But in OotS we all(?) know that Haley's armor "must" be a 10,000ish gold piece valued item, so such things sort of demand an explanation. Since no really natural explanation is possible, a funny one is the better choice. To be funny, it must somehow not meet our expectations. That fact that a certain kind of surprise seems to elicit comment, in my book, demonstrates the cleverness of the choice in the very commonly male-centric genre.