Hahaha, this thread is a hoot!
Jonesy, I'm so glad that you were able to bring him over to the dark side.
I think that I through a mix of luck and effort, I've managed to keep my guy from getting too worried when a giant order shows up. I've basically framed it as the best option for him to have a say in what I wear without having to go to the mall with me, and he likes that. He (luckily) likes to say what he likes and doesn't like, and to help me decide what fits best, all without leaving the couch! I also tend to emphasize what a great deal something was (I got this for 40% off!) rather than how much it cost ($135 is 40% off of $225!).
Also, I see no need to mention the dollar amount until after making returns, unless it's to point out what an absurd hassle it is to have to order so much to find the perfect items. I've ordered thousand of dollars of shoes from Zappos so far this year, but I've only kept two pairs for a total of about $200. Last year I ordered over a thousand dollars worth of bras so that I could try on everything that I was even remotely interested in, and try different sizes, and I kept two of them for a total of about $120. In the world of returns, it's only what you keep that matters!