You might laugh, but i would do all of that stuff when you make the transition.

Grow facial hair a couple of months prior, then shave it when you go to the piece. Use styling products on your hair when you normally don't use them. Go with a radically different style. Get highlights in the piece. Any and all of these things will throw people off when you make take the plunge. They will think you went on one of those makeover shows, lol