That's not a good idea - in my experience launching a redesign almost always causes a dip in conversions for the first couple of weeks before people get used to it and start buying again.
That's exactly why a slow design evolution is better than redesign for big companies.
Despite the fact my comment was mostly tongue in cheek, I don't agree with you–at least not in this sense.
Shoes aren't something that consumers buy every week. New customers to Zappos wouldn't know the difference, and I doubt repeat Zappos customers would be so confused/disoriented as to not make a purchase (or need time to get acclimated).
This reminded me of when Facebook did that redesign some months back. A lot of people I know were outraged, but then after about a week or so, they get used to it, and before long, they are back to friending people they arent really friends with. No one rags on the design now. To be honest, I can not even recall what the old design looked like anymore...
Googles slight redesign had the same effect on me. I was displeased at first, but now I'm just used to it and I have moved on with my life.
If the redesign gets more sales/conversions than normal, Andrew gets to keep the extra money ... if not, he has to pay the difference :)